US11884839B2 - Acetal-protected silanol group-containing polysiloxane composition - Google Patents
Acetal-protected silanol group-containing polysiloxane composition Download PDFInfo
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- US11884839B2 US11884839B2 US16/329,175 US201716329175A US11884839B2 US 11884839 B2 US11884839 B2 US 11884839B2 US 201716329175 A US201716329175 A US 201716329175A US 11884839 B2 US11884839 B2 US 11884839B2
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- United States
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- polysiloxane
- resist
- formula
- film
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- -1 polysiloxane Polymers 0.000 title claims abstract description 503
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 191
- 239000000203 mixture Substances 0.000 title claims abstract description 118
- 125000005372 silanol group Chemical group 0.000 title claims abstract description 52
- 229910000077 silane Inorganic materials 0.000 claims abstract description 76
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000008199 coating composition Substances 0.000 claims abstract description 65
- 239000000758 substrate Substances 0.000 claims abstract description 61
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 58
- 125000004036 acetal group Chemical group 0.000 claims abstract description 48
- 238000005530 etching Methods 0.000 claims abstract description 44
- 239000007859 condensation product Substances 0.000 claims abstract description 41
- 239000004065 semiconductor Substances 0.000 claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 claims abstract description 23
- 125000000962 organic group Chemical group 0.000 claims abstract description 20
- 238000012545 processing Methods 0.000 claims abstract description 16
- 230000002441 reversible effect Effects 0.000 claims abstract description 13
- 229910018540 Si C Inorganic materials 0.000 claims abstract description 12
- 229910010271 silicon carbide Inorganic materials 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 51
- 229910052710 silicon Inorganic materials 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 239000010703 silicon Substances 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 30
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 28
- 230000007062 hydrolysis Effects 0.000 claims description 24
- 238000006460 hydrolysis reaction Methods 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 15
- 238000004380 ashing Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 claims description 4
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 4
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 claims description 3
- BJOWTLCTYPKRRU-UHFFFAOYSA-N 3-ethenoxyoctane Chemical compound CCCCCC(CC)OC=C BJOWTLCTYPKRRU-UHFFFAOYSA-N 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 3
- 239000010408 film Substances 0.000 description 117
- 239000000243 solution Substances 0.000 description 85
- 238000006243 chemical reaction Methods 0.000 description 74
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
- 230000015572 biosynthetic process Effects 0.000 description 56
- 238000003786 synthesis reaction Methods 0.000 description 56
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 44
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 41
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 41
- 229910052719 titanium Inorganic materials 0.000 description 41
- 239000010936 titanium Substances 0.000 description 41
- 229910052726 zirconium Inorganic materials 0.000 description 41
- 239000002904 solvent Substances 0.000 description 40
- 229920002120 photoresistant polymer Polymers 0.000 description 36
- 239000007864 aqueous solution Substances 0.000 description 35
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 35
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 33
- 238000000576 coating method Methods 0.000 description 33
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 33
- 239000007983 Tris buffer Substances 0.000 description 32
- 239000007795 chemical reaction product Substances 0.000 description 32
- 239000011248 coating agent Substances 0.000 description 32
- 239000007787 solid Substances 0.000 description 31
- 238000005259 measurement Methods 0.000 description 24
- 239000011369 resultant mixture Substances 0.000 description 24
- 239000004793 Polystyrene Substances 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 23
- 229920002223 polystyrene Polymers 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- 150000001450 anions Chemical class 0.000 description 20
- 150000001721 carbon Chemical group 0.000 description 20
- 238000001723 curing Methods 0.000 description 20
- 239000007789 gas Substances 0.000 description 20
- 239000003513 alkali Substances 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 238000011161 development Methods 0.000 description 16
- 230000018109 developmental process Effects 0.000 description 16
- 238000004090 dissolution Methods 0.000 description 16
- 125000001841 imino group Chemical group [H]N=* 0.000 description 16
- 235000011054 acetic acid Nutrition 0.000 description 15
- 125000006165 cyclic alkyl group Chemical group 0.000 description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 15
- GQKDBQTXMIUPSY-UHFFFAOYSA-N 1-methoxypropan-2-ol;1-methoxypropan-2-yl acetate Chemical compound COCC(C)O.COCC(C)OC(C)=O GQKDBQTXMIUPSY-UHFFFAOYSA-N 0.000 description 14
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 14
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 13
- 229910020175 SiOH Inorganic materials 0.000 description 13
- 239000011230 binding agent Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- 239000011148 porous material Substances 0.000 description 12
- 229940070891 pyridium Drugs 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 12
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 150000007942 carboxylates Chemical group 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 238000001312 dry etching Methods 0.000 description 9
- 238000010894 electron beam technology Methods 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 229940006460 bromide ion Drugs 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 150000003949 imides Chemical class 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 8
- 229940006461 iodide ion Drugs 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 150000003863 ammonium salts Chemical class 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000007524 organic acids Chemical class 0.000 description 7
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229940077388 benzenesulfonate Drugs 0.000 description 6
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000013522 chelant Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 6
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 6
- RLUCXJBHKHIDSP-UHFFFAOYSA-N propane-1,2-diol;propanoic acid Chemical group CCC(O)=O.CC(O)CO RLUCXJBHKHIDSP-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 6
- 150000003384 small molecules Chemical class 0.000 description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 6
- 239000012953 triphenylsulfonium Substances 0.000 description 6
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 206010034972 Photosensitivity reaction Diseases 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 5
- 150000003003 phosphines Chemical class 0.000 description 5
- 150000004714 phosphonium salts Chemical class 0.000 description 5
- 230000036211 photosensitivity Effects 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 4
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
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- XDQXIEKWEFUDFK-UHFFFAOYSA-N tributylsulfanium Chemical class CCCC[S+](CCCC)CCCC XDQXIEKWEFUDFK-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- USMVHTQGEMDHKL-UHFFFAOYSA-M triphenylsulfanium;2,4,6-tri(propan-2-yl)benzenesulfonate Chemical compound CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C(C(C)C)=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 USMVHTQGEMDHKL-UHFFFAOYSA-M 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- OOLZXLYYPCOPQZ-UHFFFAOYSA-N tripropylsulfanium Chemical class CCC[S+](CCC)CCC OOLZXLYYPCOPQZ-UHFFFAOYSA-N 0.000 description 1
- ZMOJTPABCOWEOS-UHFFFAOYSA-N tris(4-tert-butylphenyl)sulfanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[S+](C=1C=CC(=CC=1)C(C)(C)C)C1=CC=C(C(C)(C)C)C=C1 ZMOJTPABCOWEOS-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
Definitions
- the present invention relates to an acetal-protected silanol group-containing polysiloxane composition used for, for example, a photosensitive composition and a coating composition for pattern reversal for forming a fine pattern.
- a technique for forming a fine pattern on a substrate and carrying out etching along with this pattern to process the substrate is widely used in the field of semiconductor production.
- KrF excimer laser and ArF excimer laser are used and exposure techniques using electron beams and EUV (extreme ultraviolet rays) have been studied.
- a resist pattern is formed on a semiconductor substrate and the resist pattern is coated with a silicon-based coating liquid. This allows the spaces in the resist pattern to be filled with silicon-based coating liquid. Thereafter, the substrate is baked to form a coating film. Thereafter, the upper part of the silicon-containing coating film is etch-backed by etching with a fluorine-based gas to expose the upper part of the resist pattern and the resist pattern is removed with an oxygen-based etching gas, which is replaced from the fluorine-based gas. Consequently, the resist pattern disappears and the silicon-based pattern derived from the silicon-based coating film remains to reverse the pattern.
- Etching of the underlayer of the silicon-based film or the substrate using the silicon-based film in which the reversed pattern is formed as an etching mask allows the reversed pattern to be transferred and the pattern is formed on the substrate.
- Patent Document 1 a material using a polysiloxane formed by cohydrolyzing a silane having a hydrogen atom, a fluorine atom, a liner or branched alkyl group having a carbon number of 1 to 5, a cyano group, a cyanoalkyl group, an alkylcarbonyloxy group, an alkenyl group, or an aryl group with tetraethoxysilane and an ether-based solvent is utilized (Patent Document 1).
- Patent Document 2 There is also an invention in which a material produced by using a polyalkylsiloxane is utilized (Patent Document 2).
- a polysiloxane composition having a high silicon content for improving the etching resistance may frequently cause a problem of storage stability.
- the present invention includes a polysiloxane composition having a high silicon content and the inventors of the present invention have found that both of the improvement in the etching resistance and improvement in the storage stability of the composition are simultaneously satisfied by protecting the silanol groups in the polysiloxane composition with acetal groups.
- the polysiloxane composition in which the silanol groups are protected with acetal groups has photosensitivity due to including an acid generator.
- the composition formed by combing the polysiloxane composition in which the silanol groups are protected with acetal groups with a photoacid generator may also be used as a photosensitive composition (resist).
- the present invention provides a polysiloxane composition for the pattern reversal on the resist pattern and a photosensitive polysiloxane composition.
- the present invention includes a coating composition or a photosensitive composition
- a coating composition or a photosensitive composition comprising: a polysiloxane obtained from a hydrolysis-condensation product of a hydrolyzable silane having 2 to 4 hydrolyzable groups in a molecule by protecting silanol groups of the condensation product with acetal groups, in which, in the hydrolysis-condensation product, an organic group bonded to silicon atoms through Si—C bonds exists in a molar ratio of 0 ⁇ (the organic group)/(Si) ⁇ 0.29 on average.
- the present invention includes the coating composition or the photosensitive composition according to the first aspect, in which the hydrolyzable silane comprises a hydrolyzable silane of Formula (1): R 1 a Si(R 2 ) 4-a Formula (1) (in Formula (1), R 1 is an organic group having an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkoxyaryl group, an alkenyl group, an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, or a cyano group and is bonded to a silicon atom through a Si—C bond; R 2 is an alkoxy group, an acyloxy group, or a halogen group; and a is an integer of 0 to 3).
- R 1 is an organic group having an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkoxyary
- the present invention includes the coating composition or the photosensitive composition according to the second aspect, in which the hydrolyzable silane of Formula (1) comprises any of a tetraalkoxysilane in which a is 0 in Formula (1), a methyltrialkoxysilane, a vinyltrialkoxysilane, or a phenyltrialkoxysilane in which a is 1 in Formula (1), or dimethyldialkoxysilane in which a is 2 in Formula (1).
- the hydrolyzable silane of Formula (1) comprises any of a tetraalkoxysilane in which a is 0 in Formula (1), a methyltrialkoxysilane, a vinyltrialkoxysilane, or a phenyltrialkoxysilane in which a is 1 in Formula (1), or dimethyldialkoxysilane in which a is 2 in Formula (1).
- the present invention includes the coating composition or the photosensitive composition according to the second aspect, in which the hydrolyzable silane comprises a hydrolyzable silane in which a is 0 in Formula (1) in a ratio of 71 mol % to 100 mol % and a hydrolyzable silane in which a is 1 in Formula (1) in a ratio of 0 mol % to 29 mol %.
- the present invention includes the coating composition or the photosensitive composition according to the second aspect, in which the hydrolyzable silane comprises a hydrolyzable silane in which a is 0 in Formula (1) in a ratio of 85.5 mol % to 100 mol % and a hydrolyzable silane in which a is 2 in Formula (1) in a ratio of 0 mol % to 14.5 mol %.
- the present invention includes the coating composition or the photosensitive composition according to the first aspect, in which the polysiloxane obtained by protecting the silanol groups with acetal groups is a polysiloxane having a partial structure of Formula (2):
- R 1′ , R 2′ and R 3′ each are a hydrogen atom or a C 1-10 alkyl group;
- R 4′ is a C 1-10 alkyl group;
- R 2′ and R 4′ optionally form a ring by bonding to each other; and
- a mark “*” indicates a bond to an adjacent atom).
- the present invention includes the coating composition or the photosensitive composition according to the first aspect, in which acetal protection of the silanol groups is carried out using a vinyl ether of Formula (3):
- R 1a , R 2a , and R 3a each are a hydrogen atom or a C 1-10 alkyl group; R 4a is a C 1-10 alkyl group; and R 2a and R 4a optionally form a ring by bonding to each other).
- the present invention includes the coating composition or the photosensitive composition according to the seventh aspect, in which the vinyl ether of Formula (3) is ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, ethylhexyl vinyl ether, cyclohexyl vinyl ether, 3,4-dihydro-2H-pyran, or 2,3-dihydrofuran.
- the vinyl ether of Formula (3) is ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, ethylhexyl vinyl ether, cyclohexyl vinyl ether, 3,4-dihydro-2H-pyran, or 2,3-dihydrofuran.
- the present invention includes the coating composition according to any one of the first aspect to the eighth aspect, further comprising a thermal acid generator or a photoacid generator, in which the coating composition is applied onto a resist pattern or onto an organic underlayer film to which the resist pattern is transferred.
- the present invention includes the coating composition according to any one of the first aspect to the ninth aspect, further comprising one or more compounds selected from the group consisting of water, an acid, a quencher, and a curing catalyst.
- the present invention includes a resist composition formed by further comprising a photoacid generator in the coating composition according to any one of the first aspect to the eighth aspect.
- the present invention includes a method for producing a semiconductor device, the method comprising the steps of: (I) forming a pattern on a semiconductor substrate by a nano-imprinting method; (II) applying the coating composition according to any one of the first aspect to the tenth aspect onto the pattern to embed the polysiloxane; (III) curing the embedded polysiloxane and then etching or ashing the pattern formed by the nano-imprinting method to reverse the pattern; and (IV) processing the substrate using the polysiloxane film.
- the present invention includes a method for producing a semiconductor device, the method comprising the steps of: (A) forming a resist film on a semiconductor substrate; (B) exposing the resist film and developing the resist after the exposure to obtain a resist pattern; (C) applying the coating composition according to any one of the first aspect to the tenth aspect onto the patterned resist film to embed the polysiloxane; (D) curing the embedded polysiloxane and then etching or ashing the resist film to reverse the pattern; and (E) processing the substrate using the polysiloxane film.
- the present invention includes a method for producing a semiconductor device, the method comprising the steps of: (a) forming an organic underlayer film on a semiconductor substrate; (b) applying a silicon hard mask forming composition onto the organic underlayer film and baking the applied silicon hard mask forming composition to form a silicon hard mask; (c) applying a composition for a resist onto the silicon hard mask to form a resist layer; (d) exposing the resist film and developing the resist after the exposure to obtain a resist pattern; (e) applying the coating composition according to any one of the first aspect to the tenth aspect onto the resist pattern to embed the polysiloxane; (f) curing the embedded polysiloxane and then etching or ashing the resist film to reverse the pattern; (g) etching the silicon hard mask using the reversed pattern; (h) etching the organic underlayer film using the pattered silicon hard mask to form a patterned organic underlayer film; and (i) processing the substrate using the patterned organic underlayer film.
- the present invention includes a method for producing a semiconductor device, the method comprising the steps of: (1) forming an organic underlayer film on a semiconductor substrate; (2) applying a silicon hard mask forming composition onto the organic underlayer film and baking the applied silicon hard mask forming composition to form a silicon hard mask; (3) applying a composition for a resist onto the silicon hard mask to form a resist layer; (4) exposing the resist film and developing the resist after the exposure to obtain a resist pattern; (5) etching the silicon hard mask using the resist pattern; (6) etching the organic underlayer film using the pattered silicon hard mask to form a patterned organic underlayer film; (7) applying the coating composition according to any one of the first aspect to the tenth aspect onto the patterned organic underlayer film to embed the polysiloxane; (8) curing the embedded polysiloxane and then etching or ashing the organic underlayer film to reverse the pattern; and (9) processing the substrate using the polysiloxane film.
- the present invention includes a method for producing a semiconductor device, the method comprising the steps of: (i) forming a resist film on a semiconductor substrate using the resist composition according to the eleventh aspect; (ii) exposing the resist film and developing the resist after the exposure to obtain a resist pattern; and (iii) processing the substrate using the patterned resist film.
- the coating composition including the polysiloxane can be applied onto a resist pattern or a patterned organic underlayer film to which the resist pattern is transferred to embed (to fill) the coating composition between the spaces in the resist pattern or between the spaces in the pattern of the organic underlayer film without intermixing of the coating composition with the resist pattern formed on the substrate to be processed or the patterned organic underlayer film to which the resist pattern is transferred.
- the coating composition including the polysiloxane is cured to form a polysiloxane and a smooth surface can be formed later by etch back using etching (gas etching).
- the organic underlayer film can be removed by ashing (ashing process) and thus the pattern formed in the resist or the organic underlayer film can be reversed to a pattern of the polysiloxane formed by filling the coating composition including polysiloxane.
- the substrate to be processed can be processed by these reversed patterns.
- the substrate to be processed can be processed with the film having high adhesiveness by using such pattern reversal.
- the polysiloxane includes the acetal-protected silanol groups.
- the acetal groups are eliminated by the acid generated from the acid generator to generate silanol groups and crosslinking is generated due to these generated silanol groups. Protection of the silanol groups with acetal groups allows silicon to be stably included in high concentration as the composition.
- the polysiloxane can be included as the coating composition with which the resist pattern or the organic underlayer film having a pattern to which the resist pattern is transferred is coated and the photosensitive composition by utilizing such properties and thus the coating composition and the photosensitive composition have excellent properties.
- the present invention includes the coating composition or the photosensitive composition comprising: a polysiloxane obtained from a hydrolysis-condensation product of a hydrolyzable silane having 2 to 4 hydrolyzable groups in a molecule by protecting silanol groups of the condensation product with acetal groups, in which, in the hydrolysis-condensation product, an organic group bonded to silicon atoms through Si—C bonds exists in a molar ratio of 0 ⁇ (the organic group)/(Si) ⁇ 0.29 on average.
- the hydrolysis-condensation product is formed by hydrolyzing the hydrolyzable silane and condensing the resultant hydrolyzed product and is a polysiloxane.
- the organic group bonded to silicon atoms through Si—C bonds exists in a molar ratio of 0 ⁇ (the organic group)/(Si) ⁇ 0.29 on an average and the organic group is bonded to the silicon atoms in a molar ratio of 0.29 or lower. That is, the hydrolysis-condensation product has a molar ratio of 0 ⁇ (the organic group)/(Si) ⁇ 0.29.
- hydrolyzable silane a hydrolyzable silane including the hydrolyzable silane of Formula (1) may be used.
- R 1 is an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkoxyaryl group, an alkenyl group, an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, or a cyano group and is bonded to a silicon atom through a Si—C bond;
- R 2 is an alkoxy group, an acyloxy group, or a halogen group; and a is an integer of 0 to 3.
- the hydrolyzable silane may include a hydrolyzable silane in which a is 0 in Formula (1) in a ratio of 71 mol % to 100 mol % and a hydrolyzable silane in which a is 1 in Formula (1) in a ratio of 0 mol % to 29 mol %.
- the hydrolyzable silane may include a hydrolyzable silane in which a is 0 in Formula (1) in a ratio of 85.5 mol % to 100 mol % and a hydrolyzable silane in which a is 2 in Formula (1) in a ratio of 0 mol % to 14.5 mol %.
- composition including the polysiloxane according to the present invention includes the hydrolysis-condensation product of the hydrolyzable silane of Formula (1) and a solvent.
- a solvent for example, an acid, water, an alcohol, a curing catalyst, an acid generator, other organic polymers, a light absorbing compound, a surfactant, or the like may be included.
- the solid content in the composition including the polysiloxane according to the present invention is, for example, 0.1% by mass to 50% by mass, 0.1% by mass to 30% by mass, or 0.1% by mass to 25% by mass.
- the solid content is a content in which a solvent component is removed from the total components of the composition including the polysiloxane.
- the ratio of hydrolyzable silane, the hydrolysis product thereof, and the hydrolysis-condensation product thereof included in the solid content is 20% by mass or higher, for example, 50% by mass to 100% by mass, 60% by mass to 99% by mass, or 70% by mass to 99% by mass.
- the hydrolyzable silane, the hydrolysis product thereof, and the hydrolysis-condensation product thereof may also be used as a mixture of these compounds.
- the condensation product that is made by hydrolyzing the hydrolyzable silane and condensing the obtained hydrolysis product may be used.
- a partial hydrolysis product in which hydrolysis is not fully completed when the hydrolysis-condensation product is obtained and the silane compound may be mixed with the hydrolysis-condensation product and the resultant mixture may also be used.
- the condensation product is a polymer having a polysiloxane structure.
- the alkyl group is a linear or branched alkyl group having a carbon atom number of 1 to 10 and examples thereof may include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, n-hexyl, 1-methyl-n-pentyl group, 2-methyl-n-pentyl group, 3-methyl-n-pentyl group, 4-methyl-n-pentyl group, 1,1-dimethyl-n-butyl group, 1,2-di
- a cyclic alkyl group may be also used and examples of a C 1-10 cyclic alkyl group may include cyclopropyl group, cyclobutyl group, 1-methyl-cyclopropyl group, 2-methyl-cyclopropyl group, cyclopentyl group, 1-methyl-cyclobutyl group, 2-methyl-cyclobutyl group, 3-methyl-cyclobutyl group, 1,2-dimethyl-cyclopropyl group, 2,3-dimethyl-cyclopropyl group, 1-ethyl-cyclopropyl group, 2-ethyl-cyclopropyl group, cyclohexyl group, 1-methyl-cyclopentyl group, 2-methyl-cyclopentyl group, 3-methyl-cyclopentyl group, 1-ethyl-cyclobutyl group, 2-ethyl-cyclobutyl group, 3-ethyl-cyclobutyl group, 1,2-dimethyl-cyclobutyl group, 1,3-dimethyl-
- the alkenyl group is a C 2-10 alkenyl group and examples thereof may include ethenyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-ethenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 1-ethylethenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-n-propylethenyl group, 1-methyl-1-butenyl group, 1-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2-ethyl-2-propenyl group, 2-methyl-1-butenyl group, 2-methyl-2-butenyl group, 2-methyl-3-butenyl group, 3-methyl-1-butenyl group, 3-methyl-2-buten
- the aryl group includes a C 6-40 aryl group and examples thereof may include phenyl group, o-methylphenyl group, m-methylphenyl group, p-methylphenyl group, o-chlorophenyl group, m-chlorophenyl group, p-chlorophenyl group, o-fluorophenyl group, p-mercaptophenyl group, o-methoxyphenyl group, p-methoxyphenyl group, p-aminophenyl group, p-cyanophenyl group, ⁇ -naphthyl group, ⁇ -naphthyl group, o-biphenylyl group, m-biphenylyl group, p-biphenylyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group
- Examples of the organic group having an epoxy group may include glycidoxymethyl, glycidoxyethyl, glycidoxypropyl, glycidoxybutyl, and epoxycyclohexyl.
- Examples of the organic group having an acryloyl group may include acryloylmethyl, acryloylethyl, and acryloylpropyl.
- Examples of the organic group having a methacryloyl group may include methacryloylmethyl, methacryloylethyl, and methacryloylpropyl.
- Examples of the organic group having a mercapto group may include ethylmercapto, butylmercapto, hexylmercapto, and octylmercapto.
- Examples of the organic group having a cyano group may include cyanoethyl and cyanopropyl.
- Examples of a C 1-20 alkoxy group may include an alkoxy group containing linear, branched, or cyclic alkyl part having carbon atom number of 1 to 20.
- Examples of the alkoxy group containing the linear and branched alkyl part may include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, n-pentyloxy group, 1-methyl-n-butoxy group, 2-methyl-n-butoxy group, 3-methyl-n-butoxy group, 1,1-dimethyl-n-propoxy group, 1,2-dimethyl-n-propoxy group, 2,2-dimethyl-n-propoxy group, 1-ethyl-n-propoxy group, n-hexyloxy group, 1-methyl-n-pentyloxy group, 2-methyl-n-pentyloxy group, 3-methyl-n-pentyloxy group, 4-methyl
- alkoxy group containing the cyclic alkyl part may include cyclopropoxy group, cyclobutoxy group, 1-methyl-cyclopropoxy group, 2-methyl-cyclopropoxy group, cyclopentyloxy group, 1-methyl-cyclobutoxy group, 2-methyl-cyclobutoxy group, 3-methyl-cyclobutoxy group, 1,2-dimethyl-cyclopropoxy group, 2,3-dimethyl-cyclopropoxy group, 1-ethyl-cyclopropoxy group, 2-ethyl-cyclopropoxy group, cyclohexyloxy group, 1-methyl-cyclopentyloxy group, 2-methyl-cyclopentyloxy group, 3-methyl-cyclopentyloxy group, 1-ethyl-cyclobutoxy group, 2-ethyl-cyclobutoxy group, 3-ethyl-cyclobutoxy group, 1,2-dimethyl-cyclobutoxy group, 1,3-dimethyl-cyclobutoxy group, 2,2-dimethyl-cyclobutoxy group, 2,3-
- Examples of the C 2-20 acyloxy group may include methylcarbonyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group, n-butylcarbonyloxy group, i-butylcarbonyloxy group, s-butylcarbonyloxy group, t-butylcarbonyloxy group, n-pentylcarbonyloxy group, 1-methyl-n-butylcarbonyloxy group, 2-methyl-n-butylcarbonyloxy group, 3-methyl-n-butylcarbonyloxy group, 1,1-dimethyl-n-propylcarbonyloxy group, 1,2-dimethyl-n-propylcarbonyloxy group, 2,2-dimethyl-n-propylcarbonyloxy group, 1-ethyl-n-propylcarbonyloxy group, n-hexylcarbonyloxy group, 1-methyl-n-pentylcarbonyloxy
- halogen group may include fluorine, chlorine, bromine, and iodine.
- the hydrolyzable silane of Formula (1) comprises any of a tetraalkoxysilane in which a is 0 in Formula (1), a methyltrialkoxysilane, a vinyltrialkoxysilane, or a phenyltrialkoxysilane in which a is 1 in Formula (1), or dimethyldialkoxysilane in which a is 2 in Formula (1).
- the polysiloxane obtained from the hydrolysis-condensation product of the hydrolyzable silane by protecting the silanol groups of the condensation product with acetal groups may be used.
- the polysiloxane obtained by protecting the silanol groups with acetal groups is a polysiloxane having a partial structure of Formula (2).
- R 1′ , R 2′ , and R 3′ each are a hydrogen atom or a C 1-10 alkyl group; R 4′ is a C 1-10 alkyl group; and R 2′ and R 4′ optionally form a ring by bonding to each other.
- the mark “*” indicates a bond to an adjacent atom. Examples of the adjacent atom may include the oxygen atom of the siloxane bond, the oxygen atom of the silanol group, and the carbon atom originated from R 1′ of Formula (1).
- the alkyl group may be exemplified by the above examples.
- the acetal-protection of the silanol groups may be carried out using the vinyl ether of Formula (3).
- the hydrolysis-condensation product (polysiloxane) having the partial structure of Formula (2) is obtained by reacting the silanol group of the hydrolysis-condensation product of the hydrolyzable silane with the vinyl ether compound of Formula (3).
- R 1a , R 2a , and R 3a each are a hydrogen atom or a C 1-10 alkyl group;
- R 4a is a C 1-10 alkyl group; and
- R 2a and R 4a optionally form a ring by bonding to each other.
- the alkyl group may be exemplified by the above examples.
- aprotic solvents such as propylene glycol monomethyl ether acetate, ethyl acetate, dimethylformamide, tetrahydrofuran, and 1,4-dioxane may be used as the solvent.
- aprotic solvents such as propylene glycol monomethyl ether acetate, ethyl acetate, dimethylformamide, tetrahydrofuran, and 1,4-dioxane may be used as the solvent.
- pyridinium para-toluenesulfonate, trifluoromethanesulfonic acid, para-toluenesulfonic acid, methanesulfonic acid, hydrochloric acid, sulfuric acid, or the like may be used.
- Weak acids such as pyridium para-toluenesulfonate are particularly preferable.
- Examples of the vinyl ether of Formula (3) may include aliphatic vinyl ether compounds such as methyl vinyl ether, ethyl vinyl ether, isopropyl vinyl ether, normal-butyl vinyl ether, 2-ethylhexyl vinyl ether, tert-butyl vinyl ether, and cyclohexyl vinyl ether and cyclic vinyl ether compounds such as 2,3-dihydrofuran, 4-methyl-2,3-dihydrofuran, and 2,3-dihydro-4H-pyran.
- aliphatic vinyl ether compounds such as methyl vinyl ether, ethyl vinyl ether, isopropyl vinyl ether, normal-butyl vinyl ether, 2-ethylhexyl vinyl ether, tert-butyl vinyl ether, and cyclohexyl vinyl ether and cyclic vinyl ether compounds such as 2,3-dihydrofuran, 4-methyl-2,3-dihydrofuran, and 2,3-d
- ethyl vinyl ether propyl vinyl ether, butyl vinyl ether, ethylhexyl vinyl ether, cyclohexyl vinyl ether, 3,4-dihydro-2H-pyran, or 2,3-dihydrofuran can be preferably used.
- the silanol groups in the hydrolysis-condensation product of the hydrolyzable silane can be protected with acetal groups at any ratio.
- the silanol groups and the silanol groups protected with acetal groups can exist in a ratio of (acetal group)/(acetal group+silanol group) of 1 mol % to 100 mol % or 5 mol % to 85 mol %.
- hydrolysis-condensation product polysiloxane
- hydrolysis-condensation product polysiloxane
- hydrolysis-condensation product (polyorganosiloxane) of the hydrolyzable silane a condensation product having a weight average molecular weight of 1,000 to 1,000,000 or 1,000 to 100,000 can be obtained. These molecular weights are molecular weights determined by GPC analysis in terms of polystyrene.
- measurement conditions of GPC are as follows: GPC apparatus (trade name HLC-8220GPC, manufactured by Tosoh Co., Ltd), GPC column (trade name Shodex KF803L, KF802, and KF801, manufactured by Showa Denko K.K.), Column temperature at 40° C., eluent (elution solvent) of tetrahydrofuran, and flow volume (flow rate) at 1.0 ml/min.
- the measurement can be carried out using polystyrene (manufactured by Showa Denko K.K.) as a standard sample.
- an alkoxysilyl group an acyloxysilyl group, or a halogenated silyl group
- 0.5 mole to 100 moles, preferably 1 mole to 10 moles of water per 1 mole of the hydrolyzable group is used.
- the hydrolysis catalyst may be used in an amount of 0.001 mole to 10 moles and preferably 0.001 mole to 1 mole per 1 mole of the hydrolyzable group.
- the reaction temperature during the hydrolysis and condensation is usually 20° C. to 80° C.
- the hydrolysis may be complete hydrolysis or may be partial hydrolysis.
- the hydrolysis product and the monomer may remain in the hydrolysis-condensation product.
- the catalyst may be used during the hydrolysis and condensation.
- An acid or a base may be used as the hydrolysis catalyst.
- Examples of the hydrolysis catalyst may include a metal chelate compound, an organic acid, an inorganic acid, an organic base, and an inorganic base.
- Examples of the metal chelate compound as the hydrolysis catalyst may include titanium chelate compounds such as triethoxy-mono(acetylacetonate) titanium, tri-n-propoxy-mono(acetylacetonate) titanium, tri-i-propoxy-mono(acetylacetonate) titanium, tri-n-butoxy-mono(acetylacetonate) titanium, tri-sec-butoxy-mono(acetylacetonate) titanium, tri-t-butoxy-mono(acetylacetonate) titanium, diethoxy-bis(acetylacetonate) titanium, di-n-propoxy-bis(acetylacetonate) titanium, di-i-propoxy-bis(acetylacetonate) titanium, di-n-butoxy-bis(acetylacetonate) titanium, di-
- Examples of the organic acid as the hydrolysis catalyst may include acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, sebacic acid, gallic acid, butyric acid, mellitic acid, arachidonic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, linoleic acid, linolenic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, p-toluenesulfonic acid, benzenesulfonic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, formic acid, malonic acid, sulfonic acid,
- Examples of the inorganic acid as the hydrolysis catalyst may include hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, and phosphoric acid.
- Examples of the organic base as the hydrolysis catalyst may include pyridine, pyrrole, piperazine, pyrrolidine, piperidine, picoline, trimethylamine, triethylamine, monoethanolamine, diethanolamine, dimethyl-monoethanolamine, monomethyl-diethanolamine, triethanolamine, diazabicyclooctane, diazabicyclononane, diazabicycloundecene, and tetramethylammonium hydroxide.
- Examples of the inorganic base may include ammonia, sodium hydroxide, potassium hydroxide, barium hydroxide, and calcium hydroxide.
- the metal chelate compound, the organic acid, and the inorganic acid are preferable, and these catalysts may be used singly or in combination of two or more of them.
- organic solvent used for the hydrolysis may include aliphatic hydrocarbon solvents such as n-pentane, i-pentane, n-hexane, i-hexane, n-heptane, i-heptane, 2,2,4-trimethylpentane, n-octane, i-octane, cyclohexane, and methylcyclohexane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, i-propylbenzene, diethylbenzene, i-butylbenzene, triethylbenzene, di-i-propylbenzene, n-amylnaphthalene, and trimethylbenzene; monoalcohol solvents such as methanol,
- ketone solvents are preferable from the viewpoint of storage stability of the obtained solution: acetone, methylethyl ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, diethyl ketone, methyl-i-butyl ketone, methyl-n-pentyl ketone, ethyl-n-butyl ketone, methyl-n-hexyl ketone, di-i-butyl ketone, trimethyl nonanone, cyclohexanone, methylcyclohexanone, 2,4-pentanedione, acetonylacetone, diacetone alcohol, acetophenone, and fenchone.
- the coating composition including the polysiloxane according to the present invention may include a curing catalyst.
- the curing catalyst acts as a curing catalyst when a coating film containing a polyorganosiloxane made of the hydrolysis-condensation product is heated and cured.
- Examples of the curing catalyst may include ammonium salts, phosphines, phosphonium salts, and sulfonium salts.
- ammonium salt may include a quaternary ammonium salt having a structure of Formula (D-1):
- a quaternary ammonium salt having a structure of (D-2): R 22 R 23 R 24 R 25 N + Y ⁇ Formula (D-2) (wherein R 22 , R 23 , R 24 , and R 25 are alkyl groups or aryl groups; N is a nitrogen atom; Y ⁇ is an anion; and R 22 , R 23 , R 24 , and R 25 each are bonded to the nitrogen atom through a C—N bond),
- R 29 and R 30 are alkyl groups or aryl groups, and Y ⁇ is an anion
- Examples of the phosphonium salts may include a quaternary phosphonium salt of Formula (D-7): R 31 R 32 R 33 R 34 P + Y ⁇ Formula (D-7) (wherein R 31 , R 32 , R 33 , and R 34 are alkyl groups or aryl groups; P is a phosphorus atom; Y ⁇ is an anion, and R 31 , R 32 , R 33 , and R 34 each are bonded to the phosphorus atom through a C—P bond).
- D-7 quaternary phosphonium salt of Formula (D-7): R 31 R 32 R 33 R 34 P + Y ⁇ Formula (D-7) (wherein R 31 , R 32 , R 33 , and R 34 are alkyl groups or aryl groups; P is a phosphorus atom; Y ⁇ is an anion, and R 31 , R 32 , R 33 , and R 34 each are bonded to the phosphorus atom through a C—P bond).
- Examples of the sulfonium salts may include a tertiary sulfonium salt of Formula (D-8): R 35 R 36 R 37 S + Y ⁇ Formula (D-8) (wherein R 35 , R 36 , and R 37 are alkyl groups or aryl groups; S is a sulfur atom; Y ⁇ is an anion, and R 35 , R 36 , and R 37 each are bonded to the sulfur atom through a C—S bond).
- the compound of Formula (D-1) is a quaternary ammonium salt derived from an amine.
- m is an integer of 2 to 11 and n is an integer of 2 or 3.
- R 21 in the quaternary ammonium salt is a C 1-18 alkyl group or aryl group and preferably C 2-10 alkyl group or aryl group. Examples of R 21 may include linear alkyl groups such as ethyl group, propyl group, and butyl group, and benzyl group, cyclohexyl group, cyclohexylmethyl group, and di-cyclopentadienyl group.
- Examples of the anion (Y ⁇ ) may include halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ ), and acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ )
- acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- the compound of Formula (D-2) is a quaternary ammonium salt of R 22 R 23 R 24 R 25 N + Y ⁇ .
- R 22 , R 23 , R 24 , and R 25 in the quaternary ammonium salt are a C 1-18 alkyl group or aryl group or a silane compound bonding to a silicon atom through a Si—C bond.
- Examples of the anion (Y ⁇ ) may include halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ ), and acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ )
- acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- the quaternary ammonium salt is commercially available and examples of the quaternary ammonium salt may include tetramethylammonium acetate, tetrabutylammonium acetate, triethylbenzylammonium chloride, triethylbenzylammonium bromide, trioctylmethylammonium chloride, tributylbenzylammonium chloride, and trimethylbenzylammonium chloride.
- the compound of Formula (D-3) is a quaternary ammonium salt derived from 1-substituted imidazole.
- R 26 and R 27 each have a carbon number of 1 to 18 and the total carbon number of R 26 and R 27 is preferably 7 or more.
- R 26 may include methyl group, ethyl group, propyl group, phenyl group, and benzyl group and examples of R 27 may include benzyl group, octyl group, and octadecyl group.
- Examples of the anion (Y ⁇ ) may include halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ ), and acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ ), and acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- the compound is commercially available or can be produced by reacting, for example, an imidazole-based compound such as 1-methylimidazole and 1-benzylimidazole with a halogenated alkyl or a
- the compound of Formula (D-4) is a quaternary ammonium salt derived from pyridine.
- R 28 is a C 1-18 alkyl group or aryl group and preferably a C 4-18 alkyl group or aryl group. Examples of R 28 may include butyl group, octyl group, benzyl group, and lauryl group.
- Examples of the anion (Y ⁇ ) may include halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ ), and acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- the compound is commercially available or can be produced by reacting, for example, pyridine with a halogenated alkyl or a halogenated aryl such as lauryl chloride, benzyl chloride, benzyl bromide, methyl bromide, and octyl bromide.
- Examples of the compound may include N-laurylpyridinium chloride and N-benzylpyridinium bromide.
- the compound of Formula (D-5) is a quaternary ammonium salt derived from a substituted pyridine such as picoline and the like.
- R 29 is a C 1-18 alkyl group or aryl group and preferably a C 4-18 alkyl group or aryl group. Examples of R 29 may include methyl group, octyl group, lauryl group and benzyl group.
- R 30 is a C 1-18 alkyl group or aryl group and, for example, is methyl group in the case where the compound is a quaternary ammonium derived from picoline.
- Examples of the anion (Y ⁇ ) may include halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ ), and acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ )
- acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- the compound is commercially available or can be produced by reacting, for example, a substituted pyridine such as picoline with a halogenated alkyl or a halogenated aryl such as methyl bromide, octyl bromide, lauryl chloride, benzyl chloride, and benzyl bromide.
- a substituted pyridine such as picoline
- a halogenated alkyl or a halogenated aryl such as methyl bromide, octyl bromide, lauryl chloride, benzyl chloride, and benzyl bromide.
- Examples of the compound may include N-benzylpicolinium chloride, N-benzylpicolinium bromide, and N-laurylpicolinium chloride.
- the compound of Formula (D-6) is a tertiary ammonium salt derived from an amine.
- m is an integer of 2 to 11 and n is an integer of 2 or 3.
- the anion (Y ⁇ ) may include halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ ), and acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- the compound can be produced by reacting an amine with a weak acid such as a carboxylic acid and phenol.
- Example of the carboxylic acid may include formic acid and acetic acid.
- the anion (Y ⁇ ) is (HCOO ⁇ )
- the anion (Y ⁇ ) is (CH 3 COO ⁇ )
- the anion (Y ⁇ ) is (C 6 H 5 O ⁇ ).
- the compound of Formula (D-7) is a quaternary phosphonium salt having a structure of R 31 R 32 R 33 R 34 P + Y ⁇ .
- R 31 , R 32 , R 33 , and R 34 are C 1-18 alkyl groups or aryl groups or a silane compound bonding to a silicon atom through a Si—C bond.
- Preferably three substituents out of the four substituents of R 31 to R 34 are phenyl groups or substituted phenyl groups, and examples of the phenyl groups or substituted phenyl groups may include phenyl group and tolyl group.
- Remaining one substituent is a C 1-18 alkyl group or aryl group or a silane compound bonding to a silicon atom through a Si—C bond.
- the anion (Y ⁇ ) may include halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ ), and acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), and alcoholate (—O ⁇ ).
- the compound is commercially available and examples of the compound may include halogenated tetraalkylphosphoniums such as a halogenated tetra-n-butylphosphonium and a halogenated tetra-n-propylphosphonium; halogenated trialkylbenzylphosphoniums such as a halogenated triethylbenzylphosphonium; halogenated triphenyl-mono-alkylphosphoniums such as a halogenated triphenylmethylphosphonium and a halogenated triphenylethylphosphonium; a halogenated triphenylbenzylphosphonium, a halogenated tetraphenylphosphonium, a halogenated tritolyl-mono-arylphosphonium, or a halogenated tritolyl-mono-alkylphosphonium (the halogen atom is a chlorine atom or bromine atom).
- halogenated triphenyl-mono-alkylphosphoniums such as the halogenated triphenylmethylphosphonium and the halogenated triphenylethylphosphonium; halogenated triphenyl-mono-arylphosphoniums such as the halogenated triphenylbenzylphosphonium; halogenated tritolyl-mono-arylphosphoniums such as the halogenated tritolyl-mono-phenylphosphonium; and halogenated tritolyl-mono-alkylphosphoniums such as the halogenated tritolyl-mono-methylphosphonium (the halogen atom is a chlorine atom or bromine atom) are preferable.
- phosphines may include primary phosphines such as methylphosphine, ethylphosphine, propylphosphine, isopropylphosphine, isobutylphosphine, and phenylphosphine; secondary phosphines such as dimethylphosphine, diethylphosphine, diisopropylphosphine, diisoamylphosphine, and diphenylphosphine; and tertiary phosphines such as trimethylphosphine, triethylphosphine, triphenylphosphine, methyldiphenylphosphine, and dimethylphenylphosphine.
- primary phosphines such as methylphosphine, ethylphosphine, propylphosphine, isopropylphosphine, isobutylphosphine, and phenylphos
- the compound of Formula (D-8) is a tertially sulfonium salts having a structure of R 35 R 36 R 37 S + Y ⁇ .
- R 35 , R 36 , and R 37 are C 1-18 alkyl groups or aryl groups or a silane compound bonding to a silicon atom through a Si—C bond.
- two substituents out of the three substituents of R 35 to R 37 are phenyl groups or substituted phenyl groups, and examples of phenyl groups or substituted phenyl groups may include phenyl group and tolyl group. Remaining one substituent is a C 1-18 alkyl group or aryl group.
- Examples of the anion (Y ⁇ ) may include halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ ), and acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), alcoholate (—O ⁇ ), maleate anion, and nitrate anion.
- halogen ions such as a chlorine ion (Cl ⁇ ), a bromide ion (Br ⁇ ), and an iodide ion (I ⁇ )
- acid groups such as carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), alcoholate (—O ⁇ ), maleate anion, and nitrate anion.
- the compound is commercially available and examples of the compound may include halogenated tetraalkylsulfoniums such as a halogenated tri-n-butylsulfonium and a halogenated tri-n-propylsulfonium; halogenated trialkylbenzylsulfoniums such as a halogenated diethylbenzylsulfonium; halogenated diphenyl-mono-alkylsulfoniums such as a halogenated diphenylmethylsulfonium and a halogenated diphenylethylsulfonium; a halogenated triphenylsulfonium (the halogen atom is a chlorine atom or bromine atom), trialkylsulfonium carboxylates such as tri-n-butylsulfonium carboxylate and tri-n-propylsulfonium carboxylate; dialkylbenzylsul
- a nitrogen-containing silane compound can be added as a curing catalyst.
- the nitrogen-containing silane compound may include imidazole ring-containing silane compounds such as N-(3-triethoxysilypropyl)-4,5-dihydroimidazole.
- the amount of the curing catalyst is 0.01 part by mass to 10 parts by mass, 0.01 part by mass to 5 parts by mass, or 0.01 part by mass to 3 parts by mass relative to 100 parts by mass of the polyorganosiloxane.
- the hydrolyzable silane can be hydrolyzed and condensed in the solvent using the catalyst.
- Alcohols as by-products, the used hydrolysis catalyst, and water can be simultaneously removed from the obtained hydrolysis-condensation product (a polymer) by distillation under reduced pressure or other operations.
- the acid catalyst and the basic catalyst used for the hydrolysis can be removed by neutralization or ion exchange.
- an organic acid, water, an alcohol, or a combination thereof can be added in order to stabilize the coating composition including the hydrolysis-condensation product (polysiloxane).
- Examples of the organic acid may include oxalic acid, malonic acid, methylmalonic acid, succinic acid, maleic acid, malic acid, tartaric acid, phthalic acid, citric acid, glutaric acid, lactic acid, and salicylic acid. Of these organic acids, oxalic acid and maleic acid are preferable.
- the amount of the organic acid to be added is 0.1 part by mass to 5.0 parts by mass relative to 100 parts by mass of the condensation product (polyorganosiloxane).
- As water to be added pure water, ultrapure water, ion-exchanged water, and the like may be used.
- An amount of the water to be added may be 1 part by mass to 20 parts by mass relative to 100 parts of the coating composition including the polysiloxane.
- the alcohol to be added an alcohol that is easy to be evaporated by heating after application is preferable.
- the alcohol may include methanol, ethanol, propanol, isopropanol (2-propanol), and butanol.
- the amount of the alcohol to be added may be 1 part by mass to 20 parts by mass relative to 100 parts by mass of the coating composition including the polysiloxane.
- the coating composition including the polysiloxane may include one or more compounds selected from the group consisting of water, the acid, the quencher, and the curing catalyst.
- the coating composition including the polysiloxane according to the present invention may include, for example, an organic polymer compound, a photoacid generator, and a surfactant, if necessary.
- organic polymer compound allows a dry etching rate (a decreased amount in a film thickness per unit time), an attenuation coefficient, and a refractive index of the resist underlayer film formed from the coating composition including the polysiloxane according to the present invention to be controlled.
- the composition includes a compound that generates an acid in response to actinic rays or radiation rays (photoacid generator) when the present invention is used for the coating composition, in particular, a radiation sensitive composition (resist composition).
- photoacid generator a compound that generates an acid in response to actinic rays or radiation rays
- resist composition a radiation sensitive composition
- any compound may be used as long as the compound generates an acid by irradiation with high energy rays.
- Suitable photoacid generators may include sulfonium salts, iodonium salts, sulfonyldiazomethane, N-sulfonyloxyimide, and oxime-O-sulfonate type acid generators. As will be described in detail below, these compounds may be used singly or in combination of two or more of the compounds.
- the sulfonium salt is a salt of a sulfonium cation and a sulfonate, bis(substituted alkylsulfonyl)imide, or tris(substituted alkylsulfonyl)methide.
- Examples of the sulfonium cation may include triphenylsulfonium, (4-tert-butoxyphenyl)diphenylsulfonium, bis(4-tert-butoxyphenyl)phenylsulfonium, tris(4-tert-butoxyphenyl)sulfonium, (3-tert-butoxyphenyl)diphenylsulfonium, bis(3-tert-butoxyphenyl)phenylsulfonium, tris(3-tert-butoxyphenyl)sulfonium, (3,4-di-tert-butoxyphenyl)diphenylsulfonium, bis(3,4-di-tert-butoxyphenyl)phenylsulfonium, tris(3,4-di-tert-butoxyphenyl)sulfonium, diphenyl(4-thiophenoxyphenyl) sulfonium, (4-tert-but
- sulfonate may include trifluoromethanesulfonate, pentafluoroethanesulfonate, nonafluorobutanesulfonate, dodecafluorohexanesulfonate, pentafluoroethylperfluorocyclohexanesulfonate, heptadecafluorooctanesulfonate, 2,2,2-trifluoroethanesulfonate, pentafluorobenzenesulfonate, 4-trifluoromethylbenzenesulfonate, 4-fluorobenzenesulfonate, mesitylenesulfonate, 2,4,6-triisopropylbenzenesulfonate, toluenesulfonate, benzenesulfonate, 4-(4′-toluenesulfonyloxy)benzenesulfonate, naphthalenesulf
- Examples of the bis(substituted alkylsulfonyl) imide may include bistrifluoromethylsulfonylimide, bispentafluoroethylsulfonylimide, bisheptafluoropropylsulfonylimide, and 1,3-propylenebissulfonylimide.
- Examples of tris(substituted alkylsulfonyl)methide may include tristrifluoromethylsulfonylmethide.
- the sulfonium salts may include sulfonium salts made by combining these groups.
- the iodonium salt is a salt made of an iodonium cation and a sulfonate, bis(substituted alkylsulfonyl)imide, or tris(substituted alkylsulfonyl)methide.
- Examples of the iodonium cation may include aryliodonium cations such as diphenyliodonium, bis(4-tert-butylphenyl)iodonium, 4-tert-butoxyphenylphenyliodonium, and 4-methoxyphenylphenyliodonium.
- aryliodonium cations such as diphenyliodonium, bis(4-tert-butylphenyl)iodonium, 4-tert-butoxyphenylphenyliodonium, and 4-methoxyphenylphenyliodonium.
- the above are presented as examples of the sulfonate, the bis(substituted alkylsulfonyl)imide, or the tris(substituted alkylsulfonyl)methide.
- the iodonium salts may include iodonium salts made by combining these groups.
- sulfonyldiazomethane may include bissulfonyldiazomethanes and sulfonyl-carbonyldiazomethanes such as bis(ethylsulfonyl)diazomethane, bis(1-methylpropylsulfonyl)diazomethane, bis(2-methylpropylsulfonyl)diazomethane, bis(1,1-dimethylethylsulfonyl)diazomethane, bis(cyclohexylsulfonyl)diazomethane, bis(perfluoroisopropylsulfonyl)diazomethane, bis(phenylsulfonyl)diazomethane, bis(4-methylphenylsulfonyl)diazomethane, bis(2,4-dimethylphenylsulfonyl)diazomethane, bis(2,
- N-sulfonyloxyimide type photoacid generator may include a combination of an imide skeleton such as succinimide, naphthalenedicarboxylic acid imide, phthalic acid imide, cyclohexyldicarboxylic acid imide, 5-norbornene-2,3-dicarboxylic acid imide, and 7-oxabicyclo[2.2. 1]-5-heptene-2,3-dicarboxylic acid imide and a sulfonate.
- an imide skeleton such as succinimide, naphthalenedicarboxylic acid imide, phthalic acid imide, cyclohexyldicarboxylic acid imide, 5-norbornene-2,3-dicarboxylic acid imide, and 7-oxabicyclo[2.2. 1]-5-heptene-2,3-dicarboxylic acid imide and a sulfonate.
- sulfonate may include trifluoromethanesulfonate, pentafluoroethanesulfonate, nonafluorobutanesulfonate, dodecafluorohexanesulfonate, pentafluoroethylperfluorocyclohexanesulfonate, heptadecafluorooctanesulfonate, 2,2,2-trifluoroethanesulfonate, pentafluorobenzenesulfonate, 4-trifluoromethylbenzenesulfonate, 4-fluorobenzenesulfonate, mesitylenesulfonate, 2,4,6-triisopropylbenzenesulfonate, toluenesulfonate, benzenesulfonate, naphthalenesulfonate, camphorsulfonate, octanesulfonate, dodecyl
- benzoin sulfonate type photoacid generator may include benzoin tosylate, benzoin mesylate, and benzoin butanesulfonate.
- Examples of the pyrogallol trisulfonate type photoacid generator may include compounds in which all the hydroxy groups in pyrogallol, phlorogricinol, catechol, resorcinol, or hydroquinone are substituted with the following groups.
- substituent may include trifluoromethanesulfonate, pentafluoroethanesulfonate, nonafluorobutanesulfonate, dodecafluorohexanesulfonate, pentafluoroethylperfluorocyclohexanesulfonate, heptadecafluorooctanesulfonate, 2,2,2-trifluoroethanesulfonate, pentafluorobenzenesulfonate, 4-trifluoromethylbenzenesulfonate, 4-fluorobenzenesulfonate, toluenesulfonate, benzenesulfonate, naphthalenesulfonate, camphorsulfonate, octanesulfonate, dodecylbenzenesulfonate, butanesulfonate, methanesulfonate, 2-benzoyloxy-1
- Examples of the sulfone type photoacid generators may include bis(phenylsulfonyl) methane, bis(4-methylphenylsulfonyl)methane, bis(2-naphthylsulfonyl)methane, 2,2-bis(phenylsulfonyl)propane, 2,2-bis (4-methylphenylsulfonyl)propane, 2,2-bis(2-naphthylsulfonyl)propane, 2-methyl-2-(p-toluenesulfonyl)propiophenone, 2-cyclohexylcarbonyl-2-(p-toluenesulfonyl)propane, and 2,4-dimethyl-2-(p-toluenesulfonyl)pentan-3-one.
- Examples of the glyoxime derivative type photoacid generators may include bis-O-(p-toluenesulfonyl)- ⁇ -dimethylglyoxime, bis-O-(p-toluenesulfonyl)- ⁇ -diphenylglyoxime, bis-O-(p-toluenesulfonyl)- ⁇ -dicyclohexylglyoxime, bis-O-(p-toluenesulfonyl)-2,3-pentanedioneglyoxime, bis-O-(n-butanesulfonyl)- ⁇ -dimethylglyoxime, bis-O-(n-butanesulfonyl)- ⁇ -diphenylglyoxime, bis-O-(n-butanesulfonyl)- ⁇ -dicyclohexylglyoxime, bis-O-(methanesulfonyl)- ⁇ -dimethyl
- oxime sulfonates may include, in particular, (5-(4-toluenesulfonyl)oxyimino-5H-thiophen-2-ylidene)phenylacetonitrile, (5-(10-camphorsulfonyl)oxyimino-5H-thiophen-2-ylidene)phenylacetonitrile, (5-n-octanesulfonyloxyimino-5H-thiophen-2-ylidene)phenylacetonitrile, (5-(4-toluenesulfonyl)oxyimino-5H-thiophen-2-ylidene)(2-methylphenyl)acetonitrile, (5-(10-camphorsulfonyl)oxyimino-5H-thiophen-2-ylidene)(2-methylphenyl)acetonitrile, and (5-n-octanesulfonyloxyimino-5H-thiophen-2-
- oxime sulfonates may include, in particular, 2,2,2-trifluoro-1-phenyl-ethanoneoxime-O-methylsulfonate, 2,2,2-trifluoro-1-phenyl-ethanoneoxime-O-(10-camphorylsulfonate), 2,2,2-trifluoro-1-phenyl-ethanoneoxime-O-(4-methoxyphenylsulfonate), 2,2,2-trifluoro-1-phenyl-ethanoneoxime-O-(1-naphthylsulfonate), 2,2,2-trifluoro-1-phenyl-ethanoneoxime-O-(2-naphthylsulfonate), 2,2,2-trifluoro-1-phenyl-ethanoneoxime-O-(2,4,6-trimethylphenylsulfonate), 2,2,2-trifluoro-1-(4-methylphenyl)-ethanoneoxime-O-(10-campho
- Examples of the oxime sulfonate may include ⁇ -(p-toluenesulfonyloxyimino)-phenylacetonitrile, ⁇ -(p-chlorobenzenesulfonyloxyimino)-phenylacetonitrile, ⁇ -(4-nitrobenzenesulfonyloxyimino)-phenylacetonitrile, ⁇ -(4-nitro-2-trifluoromethylbenzenesulfonyloxyimino)-phenylacetonitrile, ⁇ -(benzenesulfonyloxyimino)-4-chlorophenylacetonitrile, ⁇ -(benzenesulfonyloxyimino)-2,4-dichlorophenylacetonitrile, ⁇ -(benzenesulfonyloxyimino)-2,6-dichlorophenylacetonitrile, ⁇ -(benzenesulfon
- Examples of the oxime sulfonates may also specifically include 2-[2,2,3,3,4,4,5,5-octafluoro-1-(nonafluorobutylsulfonyloxyimino)-pentyl]-fluorene, 2-[2,2,3,3,4,4-pentafluoro-1-(nonafluorobutylsulfonyloxyimino)-butyl]-fluorene, 2-[2,2,3,3,4,4,5,5,6,6-decafluoro-1-(nonafluorobutylsulfonyloxyimino)-hexyl]-fluorene, 2-[2,2,3,3,4,4,5,5-octafluoro-1-(nonafluorobutylsulfonyloxyimino)-pentyl]-4-biphenyl, 2-[2,2,3,3,4,4-pentafluoro-1-(nonafluorobutyls
- bisoximesulfonates may particularly include bis( ⁇ -(4-toluenesulfonyloxy)imino)-p-phenylenediacetonitrile, bis( ⁇ -(benzenesulfonyloxy)imino)-p-phenylenediacetonitrile, bis( ⁇ -(methanesulfonyloxy)imino)-p-phenylenediacetonitrile, bis( ⁇ -(butanesulfonyloxy)imino)-p-phenylenediacetonitrile, bis( ⁇ -(10-camphorsulfonyloxy)imino)-p-phenylenediacetonitrile, bis( ⁇ -(4-toluenesulfonyloxy)imino)-p-phenylenediacetonitrile, bis( ⁇ -(trifluoromethanesulfonyloxy)imino)-p-phenylenediacetonitrile, bis(
- the sulfonium salts, the bissulfonyldiazomethanes, the N-sulfonyloxyimide, the oxime-O-sulfonates, and the glyoxime derivatives are preferably used.
- the sulfonium salts, the bissulfonyldiazomethanes, the N-sulfonyloxyimide, and the oxime-O-sulfonates are more preferably used as the photoacid generator.
- the preferable photoacid generator may include triphenylsulfonium p-toluenesulfonate, triphenylsulfonium camphorsulfonate, triphenylsulfonium pentafluorobenzenesulfonate, triphenylsulfonium nonafluorobutanesulfonate, triphenylsulfonium 4-(4′-toluenesulfonyloxy)benzenesulfonate, triphenylsulfonium-2,4,6-triisopropylbenzenesulfonate, 4-tert-butoxyphenyldiphenylsulfonium p-toluenesulfonate, 4-tert-butoxyphenyldiphenylsulfonium camphorsulfonate, 4-tert-butoxyphenyldiphenylsulfonium 4-(4′-toluenesulfonyl
- examples of the photoacid generator included in the coating composition including the polysiloxane according to the present invention may include onium salt compounds, sulfonimide compounds, and disulfonyldiazomethane compounds.
- onium salt compound may include iodonium salt compounds such as diphenyliodonium hexafluorophosphate, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-normal-butanesulfonate, diphenyliodonium perfluoro-normal-octanesulfonate, diphenyliodonium camphorsulfonate, bis(4-tert-butylphenyl)iodonium camphorsulfonate, and bis(4-tert-butylphenyl)iodonium trifluoromethanesulfonate and sulfonium salt compounds such as triphenylsulfonium hexafluoroantimonate, triphenylsulfonium nonafluoro-normal-butanesulfonate, triphenylsulfonium camphorsulfonate, and triphenyl
- sulfonimide compounds may include N-(trifluoromethanesulfonyloxy) succinimide, N-(nonafluoro-normal-butanesulfonyloxy)succinimide, N-(camphorsulfonyloxy)succinimide, and N-(trifluoromethanesulfonyloxy)naphthalimide.
- disulfonyldiazomethane compounds may include bis(trifluoromethylsulfonyl)diazomethane, bis(cyclohexylsulfonyl)diazomethane, bis(phenylsulfonyl)diazomethane, bis(p-toluenesulfonyl)diazomethane, bis(2,4-dimethylbenzenesulfonyl)diazomethane, and methylsulfonyl-p-toluenesulfonyldiazomethane.
- photoacid generators may be used singly or in combination of two or more of the photoacid generators.
- the ratio of the photoacid generator is 0.01 part by mass to 30 parts by mass, 0.01 part by mass to 15 parts by mass, or 0.1 part by mass to 10 parts by mass relative to 100 parts by mass of the condensation product (polyorganosiloxane) in the case where the photoacid generator is used.
- a thermal acid generator may be added in the case where the composition is used as the coating composition.
- the thermal acid generator may include onium salts such as ammonium salts, sulfonium salts, and phosphonium salt and the counter anion may include sulfonate, antimonate, and phosphate.
- the ammonium salt of trifluoromethanesulfonic acid is particularly preferable.
- thermal acid generators may be used singly or in combination of two or more of the thermal acid generators.
- the ratio of the thermal acid generator is 0.01 part by mass to 30 parts by mass, 0.01 part by mass to 15 parts by mass, or 0.1 part by mass to 10 parts by mass relative to 100 parts by mass of the condensation product (polyorganosiloxane) in the case where the thermal acid generator is used.
- One or more nitrogen-containing organic compounds may be blended as a basic compound (quencher) in the case where the composition according to the present invention is used as a resist composition.
- the ratio of the quencher is 0.01 part by mass to 30 parts by mass, 0.01 part by mass to 15 parts by mass, or 0.1 part by mass to 10 parts by mass relative to 100 parts by mass of the condensation product (polyorganosiloxane) in the case where the quencher is used.
- a compound that can reduce the diffusion rate during the diffusion of the acid generated from the acid generator into the resist film is suitable as the nitrogen-containing organic compound. Addition of the nitrogen-containing organic compound allows the diffusion rate of the acid in the resist film to be reduced, the resolution to be improved, the change in sensitivity after exposure to be reduced, dependency of the substrate or environment to be reduced, and the exposure margin and pattern profiles to be improved.
- Examples of such a nitrogen-containing organic compound may include primary, secondary, and tertiary aliphatic amines, mixed amines, aromatic amines, heterocyclic amines, nitrogen-containing compounds having a carboxy group, nitrogen-containing compounds having a sulfonyl group, nitrogen-containing compounds having a hydroxy group, nitrogen-containing compounds having a hydroxyphenyl group, alcoholic nitrogen-containing compounds, amides, imides, carbamates, ammonia, ammonium salts, and sulfonium salts.
- Such a nitrogen-containing organic compound may be a compound of general Formula (C-1). N(X) n (Y) 3-n Formula (C-1)
- n is an integer of 0, 1, 2, or 3.
- X may be the same as or different from each other and may be a group of Formulas (X1), (X2), or (X3).
- Y is a hydrogen atom or the same or different linear, branched, or cyclic alkyl group having a carbon atom number of 1 to 20 or 1 to 10 and may contain an ether group or a hydroxy group.
- the alkyl group may be exemplified by the above examples.
- R 200 , R 202 , and R 205 are linear or branched alkylene groups having a carbon atom number of 1 to 10
- R 201 and R 204 are hydrogen atoms, linear, branched, or cyclic alkyl groups having a carbon atom number of 1 to 20 or 1 to 10 and may include one or more hydroxy groups, ether groups, ester groups, or lactone rings.
- R 203 is a single bond or a linear or branched alkylene group having a carbon atom number of 1 to 10.
- R 206 is a linear, branched, or cyclic alkyl group having a carbon atom number of 1 to 20 or 1 to 10 and may include one or more hydroxy groups, ether groups, ester groups, or lactone rings.
- the alkyl group is as described above and the alkylene group may be a functional group derived from the alkyl group.
- the nitrogen-containing organic compounds having a cyclic structure illustrated below can be presented as examples.
- R 207 is a linear or branched alkylene group having a carbon atom number of 1 to 20, 1 to 10, or 2 to 20 and may include one or more carbonyl groups, ether groups, ester groups, or sulfide groups.
- the alkylene group is a functional group derived from the alkyl group and the alkyl group may be exemplified by the above examples.
- a nitrogen-containing organic compounds containing a cyano group can be presented as examples.
- X and R 207 are as described above and n is an integer of 1, 2, or 3.
- R 208 and R 209 are the same or different linear or branched alkylene groups having a carbon atom number of 1 to 10 or 1 to 4.
- the nitrogen-containing organic compounds having an imidazole skeleton can be presented as examples.
- R 210 is a linear, branched, or cyclic alkyl group having a carbon atom number of 1 to 20, 1 to 10, or 2 to 20 and having a polar functional group and examples of the polar functional group may include hydroxy group, carbonyl group, ester group, ether group, sulfide group, carbonate group, cyano group, or acetal group.
- R 211 , R 212 , and R 213 are hydrogen atoms, linear, branched, or cyclic alkyl groups, aryl groups, or aralkyl groups having a carbon atom number of 1 to 10.
- the nitrogen-containing organic compounds having a benzimidazole skeleton can be presented as examples.
- R 214 is a hydrogen atom, a linear, branched, or cyclic alkyl group having a carbon atom number of 1 to 10, or a C 6-40 aryl group or aralkyl group.
- R 215 is a linear, branched, or cyclic alkyl group having a carbon atom number of 1 to 20 or 1 to 10 and having a polar functional group.
- the aralkyl group is a combination of an aryl group and an alkyl group and the aryl group and alkyl group can be exemplified by the above examples.
- the polar functional group can be exemplified by the above examples.
- the nitrogen-containing organic compounds having a polar functional group can be presented as examples.
- A is a nitrogen atom or ⁇ C—R 222 and B is a nitrogen atom or ⁇ C—R 223 .
- R 216 is a linear, branched or cyclic alkyl group having a carbon atom number of 1 to 20, 1 to 10, or 2 to 20 and having a polar functional group.
- R 217 , R 218 , R 219 , and R 220 are hydrogen atoms, linear, branched, or cyclic alkyl groups having a carbon atom number of 1 to 10, or C 6-40 aryl groups.
- R 217 and R 218 , and R 219 and R 220 each may be bonded to each other to form a benzene ring, a naphthalene ring, or a pyridine ring.
- R 221 is a hydrogen atom or a linear, branched, or cyclic alkyl group or aryl group having a carbon atom number of 1 to 10.
- R 222 and R 223 are hydrogen atoms or linear, branched, or cyclic alkyl groups or aryl groups having a carbon atom number of 1 to 10.
- R 221 and R 223 may be bonded to each other to form a benzene ring or a naphthalene ring.
- the nitrogen-containing organic compounds having an aromatic carboxylic acid ester structure can be presented as examples.
- R 224 is a C 6-40 aryl group or a C 4-20 heteroaromatic group and may be substituted with a linear, branched, or cyclic alkyl group having a carbon atom number of 1 to 10 or 2 to 10, a C 6-40 aryl group, a C 7-20 aralkyl group, a C 1-10 alkoxy group, a C 1-10 acyloxy group, or a C 1-10 alkylthio group in which a part of or all of the hydrogen atoms are substituted with halogen atoms.
- R 225 is COOR 226 , OR 227 or a cyano group.
- R 226 is a C 1-10 alkyl group in which a part of methylene groups may be substituted with oxygen atoms.
- R 227 is a C 1-10 alkyl group or acyl group in which a part of methylene groups may be substituted with oxygen atoms.
- R 228 is a single bond, methylene group, ethylene group, a sulfur atom, or —O(CH 2 CH 2 O) n ⁇ group, and n is an integer of 0 to 4.
- R 229 is a hydrogen atom, methyl group, ethyl group, or phenyl group.
- X is a nitrogen atom or CR 230 .
- Y is a nitrogen atom or CR 231 .
- Z is a nitrogen atom or CR 232 .
- R 230 , R 231 and R 232 are hydrogen atoms, methyl groups, or phenyl groups, or R 230 and R 231 or R 231 and R 232 may be bonded to each other to form a heteroaromatic ring.
- the nitrogen-containing organic compounds having a 7-oxanorbornane-2-carboxylic acid ester structure can be presented as examples.
- R 233 is a hydrogen atom or a linear, branched, or cyclic alkyl group having a carbon atom number of 1 to 10.
- R 234 and R 235 each are a C 1-20 or C 1-10 alkyl group, a C 6-40 aryl group, or a C 7-20 aralkyl group that may contain a polar functional group and in which a part of the hydrogen atoms may be substituted with halogen atoms.
- R 234 and R 235 may be bonded to each other to form a C 2-20 heterocycle or heteroaromatic ring.
- the nitrogen-containing organic compounds having a group that can be eliminated by the action of an acid can be presented as examples.
- R 236 is a hydrogen atom, a C 1-10 alkyl group or cycloalkyl group, or a C 6-40 aryl group or aralkyl group. In the case where n is 2 or more, two R 236 s may be bonded to each other to form a heterocyclic hydrocarbon group.
- R 237 , R 238 and R 239 each are a hydrogen atom, a C 1-10 alkyl group or cycloalkyl group, or a C 6-40 aryl group, aralkyl group, or alkoxyalkyl group.
- n is 0 to 2 2
- m is 1 to 3, or n+m is 3.
- nitrogen-containing organic compounds can be exemplified as follows.
- Examples of primary aliphatic amines may include methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, tert-butylamine, pentylamine, tert-amylamine, cyclopentylamine, hexylamine, cyclohexylamine, heptylamine, octylamine, nonylamine, decylamine, dodecylamine, cetylamine, methylenediamine, ethylenediamine, and tetraethylenepentamine.
- Examples of the secondary aliphatic amines may include dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, diisobutylamine, di-sec-butylamine, dipentylamine, dicyclopentylamine, dihexylamine, dicyclohexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, didodecylamine, dicetylamine, N,N-dimethylmethylenediamine, N,N-dimethylethylenediamine, and N,N-dimethyltetraethylenepentamine.
- tertiary aliphatic amines may include trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tripentylamine, tricyclopentylamine, trihexylamine, tricyclohexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, tridodecylamine, tricetylamine, N,N,N′,N′-tetramethylmethylenediamine, N,N,N′,N′-tetramethylethylenediamine, and N,N,N′,N′-tetramethyltetraethylenepentamine.
- Examples of mixed amines may include dimethylethylamine, methylethylpropylamine, benzylamine, phenethylamine, and benzyldimethylamine.
- aromatic amines and heterocyclic amines may include aniline derivatives (such as aniline, N-methylaniline, N-ethylaniline, N-propylaniline, N,N-dimethylaniline, 2-methylaniline, 3-methylaniline, 4-methylaniline, ethylaniline, propylaniline, trimethylaniline, 2-nitroaniline, 3-nitroaniline, 4-nitroaniline, 2,4-dinitroaniline, 2,6-dinitroaniline, 3,5-dinitroaniline, and N, N-dimethyltoluidine), diphenyl(p-tolyl)amine, methyldiphenylamine, triphenylamine, phenylenediamine, naphthylamine, diaminonaphthalene, pyrrole derivatives (such as pyrrole, 2H-pyrrole, 1-methylpyrrole, 2,4-dimethylpyrrole, 2,5-dimethylpyrrole, and N-methylpyrrol), ox
- Examples of the nitrogen-containing compound having a carboxy group may include aminobenzoic acid, indolecarboxylic acid, and amino acid derivatives (such as nicotinic acid, alanine, arginine, aspartic acid, glutamic acid, glycine, histidine, isoleucine, glycylleucine, leucine, methionine, phenylalanine, threonine, lysine, 3-aminopyrazine-2-carboxylic acid, and methoxyalanine).
- aminobenzoic acid such as nicotinic acid, alanine, arginine, aspartic acid, glutamic acid, glycine, histidine, isoleucine, glycylleucine, leucine, methionine, phenylalanine, threonine, lysine, 3-aminopyrazine-2-carboxylic acid, and methoxyalan
- Examples of the nitrogen-containing compounds having a sulfonyl group may include 3-pyridinesulfonic acid and pyridinium p-toluenesulfonate.
- Examples of the nitrogen-containing compounds having a hydroxy group, the nitrogen-containing compounds having a hydroxyphenyl group, and the alcoholic nitrogen-containing compounds may include 2-hydroxypyridine, aminocresol, 2,4-quinolinediol, 3-indolemethanol hydrate, monoethanolamine, diethanolamine, triethanolamine, N-ethyldiethanolamine, N,N-diethylethanolamine, triisopropanolamine, 2,2′-iminodiethanol, 2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, 4-(2-hydroxyethyl)morpholine, 2-(2-hydroxyethyl)pyridine, 1-(2-hydroxyethyl)piperazine, 1-[2-(2-hydroxyethoxy)ethyl]piperazine, piperidineethanol, 1-(2-hydroxyethyl)pyrrolidine, 1-(2-hydroxyethyl)-2-pyrrolidinone, 3-piperidino-1,2-propaned
- amides may include formamide, N-methylformamide, N,N-dimethylformamide, acetamide, N-methylacetamide, N,N-dimethylacetamide, propionamide, benzamide, and 1-cyclohexylpyrrolidone.
- imides may include phthalimide, succinimide, and maleimide.
- carbamates may include N-t-butoxycarbonyl-N,N-dicyclohexylamine, N-t-butoxycarbonylbenzimidazole, and oxazolidinone.
- the sulfonium salts of sulfonic acid, nitric acid, or carboxylic acid in which the ⁇ -position is not fluorinated, the iodonium salts of sulfonic acid, nitric acid, or carboxylic acid in which the ⁇ -position is not fluorinated, the ammonium salts of sulfonic acid, nitric acid, or carboxylic acid in which the ⁇ -position is not fluorinated, and the onium salts of ammonium halides, sulfonium halides, iodonium halides, or the like may be used.
- the carboxylic acid may include maleic acid, acetic acid, propionic acid, and formic acid.
- halogen may include fluorine, chlorine, bromine, and iodine and chlorine is preferably used.
- sulfonium cation may include triphenylsulfonium, 4-hydroxyphenyldiphenylsulfonium, bis(4-hydroxyphenyl)phenylsulfonium, tris(4-hydroxyphenyl)sulfonium (4-tert-butoxyphenyl)diphenylsulfonium, bis(4-tert-butoxyphenyl)phenylsulfonium, tris(4-tert-butoxyphenyl)sulfonium, (3-tert-butoxyphenyl)diphenylsulfonium, bis(3-tert-butoxyphenyl)phenylsulfonium, tris(3-tert-butoxyphenyl)sulfonium, (3,4-di-tert-butoxyphenyl)diphenylsulfonium, bis(3,4-di-tert-butoxyphenyl)phenylsulfonium, tris(3,
- More preferable examples may include triphenylsulfonium, 4-tert-butylphenyldiphenylsulfonium, 4-tert-butoxyphenyldiphenylsulfonium, tris(4-tert-butylphenyl)sulfonium, and (4-tert-butoxycarbonylmethyloxyphenyl)diphenylsulfonium.
- more preferable examples may include 4-(methacryloyloxy)phenyldiphenylsulfonium, 4-(acryloyloxy)phenyldiphenylsulfonium, 4-(methacryloyloxy)phenyldimethylsulfonium, and 4-(acryloyloxy)phenyldimethylsulfonium.
- ammonium cations may include ammonium cations in which proton is added to a nitrogen atom of ammonia, primary, secondary, and tertiary aliphatic amines, mixed amines, aromatic amines, heterocyclic amines, nitrogen-containing compounds having a carboxy group, nitrogen-containing compounds having a sulfonyl group, nitrogen-containing compounds having a hydroxy group, nitrogen-containing compounds having a hydroxyphenyl group, and alcoholic nitrogen-containing compounds, and quaternary ammonium cations.
- Examples of quaternary ammonium cations may include tetraethylammonium and benzyltriethylammonium.
- a surfactant is effective for reducing generation of pinholes and striations during application of the coating composition including the polysiloxane according to the present invention to the substrate.
- Examples of the surfactant included in the coating composition including the polysiloxane according to the present invention may include nonionic surfactant such as polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ethers, polyoxyethylene stearyl ethers, polyoxyethylene cetyl ethers, and polyoxyethylene oleyl ethers; polyoxyethylene alkylallyl ethers such as polyoxyethylene octylphenol ethers and polyoxyethylene nonylphenol ethers; polyoxyethylene-polyoxypropylene block copolymers; sorbitan fatty acid esters such as sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and sorbitan tristearate; and polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene sorbitan monolaurates, polyoxyethylene sorbitan monopalmitates, polyoxyethylene sorbitan mono
- the ratio of the surfactant is 0.0001 part by mass to 5 parts by mass, 0.001 part by mass to 1 part by mass, or 0.01 part by mass to 1 part by mass relative to 100 parts by mass of the condensation product (polyorganosiloxane) in the case where the surfactant is used.
- a rheology modifier, an adhesion assistance agent, and the like can be added to the coating composition including the polysiloxane according to the present invention.
- the rheology modifier is effective for improving flowability of the underlayer film forming composition.
- the adhesion assistance agent is effective for improving adhesiveness between the underlayer film and the semiconductor substrate or the resist.
- any solvent may be used without particular limitation as long as the solvent can dissolve the solid content.
- the solvent may include methylcellosolve acetate, ethylcellosolve acetate, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, methyl isobutyl carbinol, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone cyclohexanone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methyl propionate, ethyl ethoxyacetate
- the organic underlayer film used in the present invention is obtained by applying and curing an organic underlayer film forming composition. Curing can be cured by heating at about 150° C. to about 230° C.
- the organic underlayer film forming composition may include a resin for coating films and solvents.
- the organic underlayer film forming composition may include a crosslinking agent, an acid, an acid generator, a light absorbing compound, and the like, if necessary.
- the resin for coating films is a resin that can mainly form films and examples of the resin may include a novolac resin, a condensed epoxy resin, a (meth)acrylic resin, a polyether resin, or a silicon-containing resin.
- the solid content of the composition is 0.1% by mass to 70% by mass or 0.1% by mass to 60% by mass.
- the solid content is a content ratio in which the solvent component is removed from the film forming composition.
- the resin for coating films may be included in the solid content in a ratio of 1% by mass to 99.9% by mass, 50% by mass to 99.9% by mass, 50% by mass to 95% by mass, or 50% by mass to 90% by mass.
- the resin for coating films has a weight average molecular weight of 600 to 1000000, or 600 to 200000.
- the silicon hard mask used in the present invention is obtained by applying and curing a silicon hard mask forming composition.
- the silicon hard mask forming composition may include a condensation product obtained by hydrolyzing the hydrolyzable silane.
- This is a polysiloxane and also includes an organopolysiloxane.
- the hydrolyzable silane can be obtained by hydrolyzing at least one hydrolyzable silane selected from the group consisting of a hydrolyzable silane having four hydrolyzable groups, a hydrolyzable silane having three hydrolyzable groups, a hydrolyzable silane having two hydrolyzable groups, and a hydrolyzable silane having one hydrolyzable group.
- the hydrolysis is carried out by adding a catalyst (for example, an acid catalyst or a basic catalyst) in an organic solvent. Thereafter, the hydrolyzed product is condensed by heating to obtain the hydrolysis-condensation product (polysiloxane or organopolysiloxane).
- the solid content of the composition is 0.1% by mass to 70% by mass or 0.1% by mass to 60% by mass.
- the solid content is a content ratio in which the solvent component is removed from the film forming composition.
- the resin for coating films may be included in the solid content in a ratio of 1% by mass to 99.9% by mass, 50% by mass to 99.9% by mass, 50% by mass to 95% by mass, or 50% by mass to 90% by mass.
- the resin for coating films has a weight average molecular weight of 600 to 1,000,000, or 600 to 200,000.
- the silicon hard mask can also be formed by vapor deposition.
- composition used in the present invention is applied onto a substrate (for example, a silicon wafer substrate, a silicon/silicon dioxide coated substrate, a silicon nitride substrate, a glass substrate, an ITO substrate, a polyimide substrate, and a low dielectric constant material (low-k material) coated substrate) used in the production of semiconductor devices by an appropriate coating method such as a method using a spinner or a coater.
- a substrate for example, a silicon wafer substrate, a silicon/silicon dioxide coated substrate, a silicon nitride substrate, a glass substrate, an ITO substrate, a polyimide substrate, and a low dielectric constant material (low-k material) coated substrate
- the applied composition is baked to form a film.
- the baking conditions are appropriately selected from a baking temperature of 80° C. to 250° C. and a baking time of 0.3 minute to 60 minutes.
- the conditions are a baking temperature of 150° C. to 250° C. and a baking time of 0.5 minute to 2 minutes.
- a film thickness of the formed film is, for example, 10 nm to 1,000 nm, 20 nm to 500 nm, 50 nm to 300 nm, or 100 nm to 200 nm.
- a photoresist layer is formed on the hard mask.
- the photoresist layer can be formed by a known method, that is, applying the photoresist composition solution onto the underlayer film and baking the applied photoresist composition.
- a thickness of the photoresist is, for example, 50 nm to 10,000 nm, 100 nm to 2,000 nm, or 200 nm to 1,000 nm.
- the organic underlayer film is formed on the substrate. Thereafter, a hard mask is formed on the organic underlayer film and the photoresist can be further applied onto the hard mask.
- the substrate can be processed by selecting an appropriate etching gas.
- the hard mask can be processed by using a fluorine-based gas serving as an etching gas, which has a sufficiently high etching rate to the photoresist
- the organic underlayer film can be processed by using an oxygen-based gas serving as an etching gas, which has a sufficiently high etching rate to the hard mask.
- the substrate can be processed by reversing the pattern.
- the photoresist is not particularly limited as long as the photoresist is sensitive to the light used for exposure. Both negative type photoresist and positive type photoresist may be used.
- the photoresist may include a positive type photoresist including a novolac resin and 1,2-naphthoquinone diazide sulfonic acid ester, a chemically amplified photoresist including a binder having a group that increases an alkali dissolution rate by decomposing with an acid and a photoacid generator, a chemically amplified photoresist including a low molecular weight compound that increases an alkali dissolution rate of the photoresist by decomposing with an acid, an alkali soluble binder, and a photo acid generator, and a chemically amplified photoresist including a binder having a group that increases an alkali dissolution rate by decomposing with an acid, a low molecular weight compound that increases an alkali dissolution rate of the photoresist
- Examples of the photoresist may include APEX-E (product name) manufactured by Shipley Company L.L.C., PAR710 (product name) manufactured by Sumitomo Chemical Co., Ltd., and SEPR 430 (product name) manufactured by Shin-Etsu Chemical Co., Ltd.
- Examples of the photoresist may also include fluorine atom-containing polymer-based photoresists described in Proc. SPIE, Vol. 3999, 330-334 (2000), Proc. SPIE, Vol. 3999, 357-364 (2000), and Proc. SPIE, Vol. 3999, 365-374 (2000).
- KrF excimer laser (a wavelength of 248 nm), ArF excimer laser (a wavelength of 193 nm), and F 2 excimer laser (a wavelength of 157 nm) can be used for the exposure.
- post exposure bake can be carried out, if necessary. The post exposure baking is carried out under appropriately selected conditions of a heating temperature of 70° C. to 150° C. and a heating time of 0.3 minute to 10 minutes.
- a resist for electron beam lithography or a resist for EUV lithography can be used instead of the photoresist as the resist.
- Both negative type electron beam resist and positive type electron beam resist can be used as the electron beam resist.
- the electron beam resist may include a chemically amplified resist including the acid generator and a binder having a group that changes an alkali dissolution rate by decomposing with an acid, a chemically amplified resist including an alkali-soluble binder, an acid generator and a low molecular weight compound that changes an alkali dissolution rate of the resist by decomposing with an acid, a chemically amplified resist including the acid generator, a binder having a group that changes an alkali dissolution rate by decomposing with an acid, and a low molecular weight compound that changes an alkali dissolution rate of the resist by decomposing with an acid, a non-chemically amplified resist including a binder having a group that changes an alkali dissolution rate by decomposing with electron beams, and
- EUV resist a methacrylate resin-based resist, a methacrylate-polyhydroxystyrene hybrid resin-based resist, and a polyhydroxystyrene resin-based resist can be used. Both negative type EUV resist and positive type EUV resist can be used as the EUV resist.
- Examples of the EUV resist may include a chemically amplified resist including the acid generator and a binder having a group that changes an alkali dissolution rate by decomposing with an acid, a chemically amplified resist including an alkali-soluble binder, an acid generator and a low molecular weight compound that changes an alkali dissolution rate of the resist by decomposing with an acid, a chemically amplified resist including the acid generator, a binder having a group that changes an alkali dissolution rate by decomposing with an acid, and a low molecular weight compound that changes an alkali dissolution rate of the resist by decomposing with an acid, a non-chemically amplified resist including a binder having a group that changes an alkali dissolution rate by decomposing with EUV light, and a non-chemically amplified resist including a binder having a moiety that is cut with EUV light and changes an alkali dissolution rate.
- a development liquid for example, an alkaline development liquid. This results in removing the exposed part of the photoresist to form a pattern of the photoresist, for example, in the case where the positive type photoresist is used.
- Examples of the development liquid may include alkali solutions such as an aqueous solution of alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, an aqueous solution of quaternary ammonium hydroxide such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, and choline, and an aqueous solution of amine such as ethanolamine, propylamine, and ethylenediamine.
- the surfactant and the like may also be added to the development liquid.
- the development conditions are appropriately selected from a temperature of 5° C. to 50° C. and a time of 10 seconds to 600 seconds.
- an organic solvent can also be used as the development liquid.
- development is carried out with a development liquid (solvent). This allows an unexposed part of the photoresist to be removed to form a pattern of the photoresist, for example, in the case where the positive type photoresist is used.
- Examples of the development liquid may include methyl acetate, butyl acetate, ethyl acetate, isopropyl acetate, amyl acetate, isoamylacetate, ethyl methoxyacetate, ethyl ethoxyacetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monopropyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monophenyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, 2-methoxy-butyl acetate, 3-methoxybutyl acetate, 4-me
- the coating composition including the polysiloxane is applied to the resist pattern and the resist pattern surface is exposed by etching back, followed by etching or ashing the resist pattern to allow the pattern to be reversed.
- the hard mask is removed by using thus formed reversed pattern as a protective film.
- the organic underlayer film (lower layer) is removed by using a film formed of the reversed pattern and the hard mask as a protective film.
- a semiconductor device can be produced by the step of processing the substrate using a patterned organic underlayer film.
- examples of the method for reversing the pattern may include a method in which the coating composition is applied onto a resist pattern and the resist pattern is etched or ashed to reverse the pattern and a method in which the coating composition is applied onto the pattern of the organic underlayer film to which the resist pattern is transferred and the organic underlayer film is etched or ashed to reverse the pattern.
- the hard mask in a part where the photoresist is removed is removed by dry etching to expose the organic underlayer film.
- gases for dry etching of the hard mask may include tetrafluoromethane (CF 4 ), perfluorocyclobutane (C 4 F 8 ), perfluoropropane (C 3 F 8 ), trifluoromethane, carbon monoxide, argon, oxygen, nitrogen, sulfur hexafluoride, difluoromethane, nitrogen trifluoride and chlorine trifluoride, chlorine, trichloroborane, and dichloroborane.
- the hard mask is preferably dry-etched by using the halogen-based gas.
- the photoresist made of organic substances is basically difficult to be removed by the dry etching using the halogen-based gas.
- the hard mask that contains many silicon atoms is rapidly removed by the halogen-based gas. Therefore, a decrease in the film thickness of the photoresist accompanying the dry etching of the hard mask can be reduced. As a result, the photoresist can be used as a thin film. Dry etching of the hard mask is preferably carried out by a fluorine-based gas.
- fluorine-based gas examples include tetrafluoromethane (CF 4 ), perfluorocyclobutane (C 4 F 8 ), perfluoropropane (C 3 F 8 ), trifluoromethane, and difluoromethane (CH 2 F 2 ).
- the organic underlayer film is removed by using a film comprising the patterned photoresist and the hard mask as a protective film.
- the organic underlayer film (lower layer) is preferably dry-etched by using an oxygen-based gas. This is because the hard mask that contains many silicon atoms is difficult to be removed by dry etching with the oxygen-based gas.
- the fluorine-based gas is used as the gas used for the etching back.
- the pattern can be reversed by etching or ashing the organic underlayer film.
- a semiconductor device can be produced by the step of processing the substrate with the reversed polysiloxane film.
- the resist pattern can be formed by the above lithography method.
- the resist pattern can also be formed by a nanoimprinting method.
- a nanoimprinting composition which is cured by heat or light is applied onto a substrate and a mold is pressed to form a resist pattern by thermosetting or photocuring.
- the semiconductor device can be produced by the steps of forming a pattern on a semiconductor substrate by a nano-imprinting method, applying the coating composition onto the pattern to embed a polysiloxane, etching or ashing the pattern formed by the nano-imprinting method to reverse the pattern, and processing the substrate using the polysiloxane film.
- a resist composition (photosensitive composition) can be made by adding the photoacid generator and, if necessary, the quencher to the composition including the polysiloxane.
- the photoacid generator, the various additives, and the solvent used in the above coating composition may be used.
- a semiconductor device can be produced by the steps of forming a resist film on a semiconductor substrate using the resist composition according to the present invention; exposing the resist film and developing the resist after the exposure to obtain a resist pattern; and processing the substrate using the patterned resist film.
- i-line wavelength 365 nm
- KrF excimer laser wavelength 248 nm
- ArF excimer laser wavelength 193 nm
- F 2 excimer laser wavelength 157 nm
- the flask containing the reaction solution was allowed to be cooled and set to an evaporator. Ethanol, which was generated during the reaction, was removed and acetone was further replaced with propylene glycol monomethyl ether acetate using the evaporator to give 248.51 g of a polysiloxane solution (corresponding to Formula (1-3)). As a result of measurement by a baking method, the solid content in the obtained reaction product was 19.9% by mass.
- the flask containing the reaction solution was allowed to be cooled and set to an evaporator. Ethanol, which was generated during the reaction, was removed and acetone was further replaced with propylene glycol monomethyl ether acetate using the evaporator to give 286.15 g of a polysiloxane solution (corresponding to Formula (1-5)). As a result of measurement by a baking method, the solid content in the obtained reaction product was 19.6% by mass.
- the solvent of the organic phase was removed using an evaporator and further replaced with propylene glycol monomethyl ether acetate to give 69.6 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 20.0% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and Table 4 and the resultant mixture was filtered through a filter having a pore size of 0.1 m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with propylene glycol monomethyl acetate to give 69.8 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 19.9% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with propylene glycol monomethyl acetate to give 52.6 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 20.0% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with propylene glycol monomethyl acetate to give 48.8 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 20.0% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with propylene glycol monomethyl acetate to give 48.7 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 20.1% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with propylene glycol monomethyl acetate to give 38.1 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-2) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-2) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 19.5% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and Table 4 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with methyl isobutyl carbinol to give 43.33 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 19.6% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with methyl isobutyl carbinol to give 165.0 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-3) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-3) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 19.3% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with propylene glycol monomethyl ether acetate to give 162.23 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-4) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-4) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 20.3% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with methyl isobutyl carbinol to give 156.62 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-5) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-5) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 19.6% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- the solvent of the organic phase was removed using an evaporator and further replaced with propylene glycol monomethyl acetate to give 53.4 g of a reaction product (polysiloxane) (the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2)).
- a reaction product polysiloxane
- the silanol groups existing in Formula (1-1) were converted into the groups of Formula (2).
- the solid content in the obtained reaction product was 19.5% by mass.
- polysiloxane was mixed with additives at the ratio listed in Table 3 and Table 4 and the resultant mixture was filtered through a filter having a pore size of 0.1 ⁇ m to give a polysiloxane composition for coating for pattern reversal.
- Example 1 and Example 2 The polysiloxane solution in which the silanol groups in the polysiloxane of Synthesis Example 10 were protected with acetal groups was used as Example 1 and Example 2 and the polysiloxane solution in which the silanol groups in the polysiloxane of Synthetic Example 1 were not protected with acetal groups was used as Comparative Example 1 and Comparative Example 2.
- These polysiloxane solutions were stored at 40° C. or 23° C. for 3 weeks and Mws (weight average molecular weights) of the stored polysiloxane solutions measured by GPC were compared.
- the polysiloxane solution in which the silanol groups were protected with acetal groups indicates less increase in Mw (weight average molecular weight) as compared with the polysiloxane solution in which the silanol groups were not protected with acetal groups and thus had excellent storage stability.
- Solutions of the polysiloxane compositions were prepared by mixing each of the polysiloxanes obtained in Synthesis Examples 10 to 19, Comparative Synthesis Example 2, and Synthesis Example 1, PAG (photoacid generator), TAG (thermal acid generator), a curing catalyst, a quencher, and a solvent in the ratio listed in Table 3 and Table 4 and filtering the resultant mixture through a fluorocarbon resin filter having a pore size of 0.1 ⁇ m.
- the addition ratio of the polymer in Table 3 and Table 4 was not the amount of the polymer solution to be added but the amount of the polymer itself to be added.
- benzyltriethylammonium chloride is abbreviated as BTEAC as the curing catalyst, triethanolamine as TEA as the quencher, propylene glycol monomethyl ether acetate as PGMEA as the solvent, propylene glycol monoethyl ether as PGEE as the solvent, propylene glycol monomethyl ether as PGME as the solvent, and methyl isobutyl carbinol as MIBC as the solvent.
- ILP-113 (trade name) is a photoacid generator manufactured by Heraeus Holding and has the following structure.
- TAG-2689 (trade name) manufactured by King Industries, Inc. was used as the thermal acid generator (its component is an ammonium salt of trifluorosulfonate) and R-30N (trade name) manufactured by DIC Corporation was used as the surfactant. Each addition amount is listed by part by mass.
- Each polysiloxane composition for coating was applied onto a wafer using a spin coater under conditions of a rotation speed of 1,500 rpm for 60 seconds and then the applied polysiloxane composition for coating was baked at 80° C. for 1 minute to form a photosensitive resin film.
- the film thickness was about 170 nm to about 190 nm.
- the sample was irradiated with broadband light from 10 mJ/cm 2 to 100 mJ/cm 2 or from 100 mJ/cm 2 to 200 mJ/cm 2 through an open mask of 1 cm ⁇ 2 cm rectangle using an automatic exposure apparatus AE810e Mask Aligner manufactured by Sanmei Co., Ltd.
- Example 10 10 mJ/cm 2 5.0 nm or less 5.0 nm or less 5.0 nm or less 20 mJ/cm 2 5.0 nm or less 5.0 nm or less 5.0 nm or less 30 mJ/cm 2 5.0 nm or less 5.0 nm or less 5.0 nm or less 40 mJ/cm 2 184.6 nm 5.0 nm or less 5.0 nm or less 50 mJ/cm 2 181.7 nm 185.4 nm 5.0 nm or less 60 mJ/cm 2 184.8 nm 171.6 nm 5.0 nm or less 70 mJ/cm 2 184.7 nm 187.4 nm 5.0 nm or less 80 mJ/cm 2 183.6 nm 187.3 nm 188.5 nm 90 mJ/cm 2 182.0 nm 185.6 nm 193.4 nm 100 mJ/cm
- Example 12 110 mJ/cm 2 5.0 nm or less 5.0 nm or less 5.0 nm or less 120 mJ/cm 2 93.3 nm 5.0 nm or less 148.0 nm 130 mJ/cm 2 184.0 nm 133.1 nm 183.3 nm 140 mJ/cm 2 189.4 nm 150.8 nm 186.6 nm 150 mJ/cm 2 190.9 nm 159.0 nm 187.7 nm 160 mJ/cm 2 189.0 nm 161.7 nm 187.1 nm 170 mJ/cm 2 188.9 nm 165.5 nm 186.1 nm 180 mJ/cm 2 187.9 nm 167.9 nm 186.2 nm 190 mJ/cm 2 188.4 nm 170.5 nm 186.8 nm 200 mJ/cm 2
- the silanol groups formed by decomposing the acetal groups with the acid generated from the photoacid generator due to exposure form polysiloxane bonds by heating after exposure and thus the polysiloxane film does not dissolve in the alkali development liquid and remains on the substrate. Therefore, it is considered that the polysiloxane composition exhibits photosensitivity.
- the siloxane coating films formed by using the compositions according to the present invention exhibit photosensitivity and excellent developability.
- Each of the solutions of the compositions including the polysiloxanes of Example 3 to Example 13 and Comparative Example 3 was applied onto a wafer by using a spin coater at a rotation speed of 1,500 rpm for 60 seconds and then baked at 80° C. for 1 minute to form a resin film. Subsequently, the entire surface of the sample was irradiated with broadband light at 200 mJ/cm 2 using an automatic exposure apparatus AE810e Mask Aligner manufactured by Sanmei Co., Ltd. equipped with Multi Light USH-250BY manufactured by USHIO Electric Co., Ltd. The irradiated sample was heated at 215° C. for 1 minute on a hot plate to prepare a polysiloxane composition film (a film thickness was adjusted to 180 nm).
- Each of the solutions of the compositions including the polysiloxanes of Example 14, Example 15, and Comparative Example 5 was applied onto a wafer by using a spin coater at a rotation speed of 1,500 rpm for 60 seconds and then baked at 215° C. for 1 minute on a hot plate to form a polysiloxane composition film (a film thickness was adjusted to 180 nm).
- the etcher used for the measurement of the dry etching rate was LAM-2300 (manufactured by Lam Research Co., Ltd.).
- Example 3 TABLE 7 Etching rate with chlorine gas
- Example 3 10.6
- Example 4 11.1
- Example 5 10.5
- Example 6 10.3
- Example 7 9.4
- Example 8 8.1
- Example 9 10.7
- Example 11 8.3
- Example 12 4.8
- Example 13 9.4 Comparative Example 3 11.2
- the siloxane coating films formed by using the compositions according to the present invention exhibit excellent etching resistance as compared with the siloxane coating films formed by using the compositions of the Comparative Examples.
- the composition exhibits excellent etching resistance during processing the substrate using the formed pattern.
- the polysiloxane composition of Example 3 was applied onto a stepped substrate having a groove having a depth of 200 nm and a width of 800 nm using a spin coater at a rotation speed of 1,500 rpm for 60 seconds and then baked at 80° C. for 1 minute to form a photosensitive resin film. Subsequently, the entire surface of the sample was irradiated with broadband light at 100 mJ/cm 2 using an automatic exposure apparatus AE810e Mask Aligner manufactured by Sanmei Co., Ltd. equipped with Multi Light USH-250BY manufactured by USHIO Electric Co., Ltd. The irradiated sample was heated at 215° C.
- Example 14 and Comparative Example 4 were applied onto the stepped substrate and baked at 215° C. for 1 minute on a hot plate to form a polysiloxane composition film (a film thickness was adjusted to 120 nm).
- the sectional shape was observed with a sectional SEM to evaluate the planarization property.
- the groove pattern having a depth of 200 nm and a width of 800 nm was observed.
- the film thicknesses at the thinnest film thickness part and the thickest film thickness part were measured with reference to the groove bottom part and the film thickness difference was calculated. As the film thickness difference becomes smaller, the planarization property becomes more excellent.
- the siloxane coating films formed by using the compositions according to the present invention exhibit the excellent planarization property as compared with the siloxane coating film formed by using the composition of the Comparative Example.
- the present invention provides the composition including the acetal-protected polysiloxane that can be used as the coating composition that forms a flat film on a substrate to be processed and carries out pattern reversal and photosensitive composition.
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- Silicon Polymers (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Paints Or Removers (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Abstract
Description
- Patent Document 1: Japanese Patent Application Publication No. 2011-118373 (JP 2011-118373 A)
- Patent Document 2: Japanese Patent Application Publication No. 2008-287176 (JP 2008-287176 A)
- Patent Document 3: Japanese Patent Application Publication No. 2009-263522 (JP 2009-263522 A)
R1 aSi(R2)4-a Formula (1)
(in Formula (1), R1 is an organic group having an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkoxyaryl group, an alkenyl group, an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, or a cyano group and is bonded to a silicon atom through a Si—C bond; R2 is an alkoxy group, an acyloxy group, or a halogen group; and a is an integer of 0 to 3).
(in Formula (2), R1′, R2′ and R3′ each are a hydrogen atom or a C1-10 alkyl group; R4′ is a C1-10 alkyl group; R2′ and R4′ optionally form a ring by bonding to each other; and a mark “*” indicates a bond to an adjacent atom).
(in Formula (3), R1a, R2a, and R3a each are a hydrogen atom or a C1-10 alkyl group; R4a is a C1-10 alkyl group; and R2a and R4a optionally form a ring by bonding to each other).
(wherein m is an integer of 2 to 11; n is an integer of 2 or 3; R21 is an alkyl group or an aryl group; and Y− is an anion),
R22R23R24R25N+Y− Formula (D-2)
(wherein R22, R23, R24, and R25 are alkyl groups or aryl groups; N is a nitrogen atom; Y− is an anion; and R22, R23, R24, and R25 each are bonded to the nitrogen atom through a C—N bond),
(wherein m is an integer of 2 to 11; n is an integer of 2 or 3; H is a hydrogen atom; and Y− is an anion).
R31R32R33R34P+Y− Formula (D-7)
(wherein R31, R32, R33, and R34 are alkyl groups or aryl groups; P is a phosphorus atom; Y− is an anion, and R31, R32, R33, and R34 each are bonded to the phosphorus atom through a C—P bond).
R35R36R37S+Y− Formula (D-8)
(wherein R35, R36, and R37 are alkyl groups or aryl groups; S is a sulfur atom; Y− is an anion, and R35, R36, and R37 each are bonded to the sulfur atom through a C—S bond).
N(X)n(Y)3-n Formula (C-1)
TABLE 1 | ||||
Example 1 | Example 2 | |||
Polymer | Synthesis Example 10 | Synthesis Example 10 | ||
Temperature | 40° C. | 23° C. | ||
Time | 3 weeks | 3 weeks | ||
Mw | 4,362 | 4,416 | ||
TABLE 2 | ||||
Comparative Example 1 | Comparative Example 2 | |||
Polymer | Synthesis Example 1 | Synthesis Example 1 | ||
Temperature | 40° C. | 23° C. | ||
Time | 3 weeks | 3 weeks | ||
Mw | Gelation | 6,527 | ||
TABLE 3 | ||||||
Curing | ||||||
catalyst | ||||||
and |
Polymer | PAG | quencher | Solvent or surfactant | |
Example 3 | Synthesis | ILP-113 | BTEAC | PGMEA | PGME | |
(part by mass) | Example 10 | 0.23 | 0.05 | 31.24 | 20.88 | |
7.52 | ||||||
Example 4 | Synthesis | ILP-113 | BTEAC | PGMEA | PGME | PGEE |
(part by mass) | Example 11 | 0.09 | 0.02 | 12.86 | 12.88 | 11.04 |
3.09 | ||||||
Example 5 | Synthesis | ILP-113 | BTEAC | PGMEA | PGME | PGEE |
(part by mass) | Example 12 | 0.09 | 0.02 | 12.88 | 12.88 | 11.04 |
3.09 | ||||||
Example 6 | Synthesis | ILP-113 | BTEAC | PGMEA | PGME | PGEE |
(part by mass) | Example 13 | 0.09 | 0.02 | 12.88 | 12.88 | 11.04 |
3.09 | ||||||
Example 7 | Synthesis | ILP-113 | BTEAC | PGMEA | PGME | PGEE |
(part by mass) | Example 14 | 0.09 | 0.02 | 12.90 | 12.88 | 11.04 |
3.09 | ||||||
Example 8 | Synthesis | ILP-113 | BTEAC | PGMEA | PGME | PGEE |
(part by mass) | Example 15 | 0.09 | 0.02 | 12.80 | 12.88 | 11.04 |
3.09 | ||||||
Example 9 | Synthesis | ILP-113 | BTEAC | PGMEA | MIBC | |
(part by mass) | Example 16 | 0.12 | 0.02 | 8.86 | 16.85 | |
4.05 | ||||||
Example 10 | Synthesis | ILP-113 | TEA | PGMEA | PGME | |
(part by mass) | Example 10 | 0.22 | 0.03 | 31.32 | 20.88 | |
7.54 | ||||||
Example 11 | Synthesis | ILP-113 | BTEAC | PGMEA | MIBC | |
(part by mass) | Example 17 | 0.20 | 0.04 | 10.32 | 32.68 | |
6.75 | ||||||
Example 12 | Synthesis | ILP-113 | BTEAC | PGMEA | PGME | |
(part by mass) | Example 18 | 0.22 | 0.05 | 31.32 | 20.88 | |
7.52 | ||||||
Example 13 | Synthesis | ILP-113 | BTEAC | PGMEA | PGME | |
(part by mass) | Example 19 | 0.20 | 0.04 | 10.75 | 32.25 | |
6.75 | ||||||
Comparative | Comparative | |||||
Example 3 | Synthesis | ILP-113 | BTEAC | PGMEA | PGME | PGEE |
(part by mass | Example 2 | 0.09 | 0.02 | 12.80 | 12.88 | 11.04 |
) | 3.09 | |||||
Comparative | Synthesis | BTEAC | PGMEA | PGME | R-30N | |
Example 4 | Example 1 | 0.01 | 13.0 | 5.58 | 0.01 | |
(part by mass) | 1.38 | |||||
TABLE 4 | |||||
Curing | |||||
Polymer | TAG | catalyst | Solvent | ||
Example 14 | Synthesis | TAG-2689 | BTEAC | PGMEA | PGME |
(part by mass) | Example 10 | 0.11 | 0.02 | 18.27 | 7.83 |
3.76 | |||||
Example 15 | Synthesis | TAG-2689 | BTEAC | PGMEA | PGME |
(part by mass) | Example 15 | 0.10 | 0.02 | 15.23 | 6.53 |
3.14 | |||||
Comparative | Comparative | TAG-2689 | BTEAC | PGMEA | PGME |
Example 5 | Synthesis | 0.11 | 0.02 | 18.27 | 7.83 |
(part by mass) | Example 2 | ||||
3.76 | |||||
TABLE 5 | |||||
Exposure mount | Example 3 | Example 9 | Example 10 | ||
10 mJ/cm2 | 5.0 nm or less | 5.0 nm or less | 5.0 nm or less | ||
20 mJ/cm2 | 5.0 nm or less | 5.0 nm or less | 5.0 nm or less | ||
30 mJ/cm2 | 5.0 nm or less | 5.0 nm or less | 5.0 nm or less | ||
40 mJ/cm2 | 184.6 nm | 5.0 nm or less | 5.0 nm or less | ||
50 mJ/cm2 | 181.7 nm | 185.4 nm | 5.0 nm or less | ||
60 mJ/cm2 | 184.8 nm | 171.6 nm | 5.0 nm or less | ||
70 mJ/cm2 | 184.7 nm | 187.4 nm | 5.0 nm or less | ||
80 mJ/cm2 | 183.6 nm | 187.3 nm | 188.5 nm | ||
90 mJ/cm2 | 182.0 nm | 185.6 nm | 193.4 nm | ||
100 mJ/cm2 | 181.2 nm | 184.8 nm | 193.4 nm | ||
TABLE 6 | |||||
Exposure mount | Example 11 | Example 12 | Example 13 | ||
110 mJ/cm2 | 5.0 nm or less | 5.0 nm or less | 5.0 nm or less | ||
120 mJ/cm2 | 93.3 nm | 5.0 nm or less | 148.0 nm | ||
130 mJ/cm2 | 184.0 nm | 133.1 nm | 183.3 nm | ||
140 mJ/cm2 | 189.4 nm | 150.8 nm | 186.6 nm | ||
150 mJ/cm2 | 190.9 nm | 159.0 nm | 187.7 nm | ||
160 mJ/cm2 | 189.0 nm | 161.7 nm | 187.1 nm | ||
170 mJ/cm2 | 188.9 nm | 165.5 nm | 186.1 nm | ||
180 mJ/cm2 | 187.9 nm | 167.9 nm | 186.2 nm | ||
190 mJ/cm2 | 188.4 nm | 170.5 nm | 186.8 nm | ||
200 mJ/cm2 | 188.2 nm | 171.3 nm | 186.5 nm | ||
TABLE 7 | |||
Etching rate with chlorine gas | |||
Example 3 | 10.6 | ||
Example 4 | 11.1 | ||
Example 5 | 10.5 | ||
Example 6 | 10.3 | ||
Example 7 | 9.4 | ||
Example 8 | 8.1 | ||
Example 9 | 10.7 | ||
Example 11 | 8.3 | ||
Example 12 | 4.8 | ||
Example 13 | 9.4 | ||
Comparative Example 3 | 11.2 | ||
TABLE 8 | |||
Etching rate with chlorine gas | |||
Example 14 | 11.8 | ||
Example 15 | 10.0 | ||
Comparative Example 5 | 13.4 | ||
TABLE 9 | |||
Film thickness difference | |||
Example 3 | 124.2 nm | ||
Example 14 | 144.1 nm | ||
Comparative example 4 | 171.8 nm | ||
Claims (13)
R1 aSi(R2)4-a Formula (1)
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